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(2S)-2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1-Pyrrolidinecarboxylic acid phenylmethyl ester

(2S)-2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1-Pyrrolidinecarboxylic acid phenylmethyl ester Structure
CAS No.
1420478-88-1
Chemical Name:
(2S)-2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1-Pyrrolidinecarboxylic acid phenylmethyl ester
Synonyms
EOS-60755;ACP-196-1;Acalabrutinib Intermediate 1;(S)-Benzyl 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin;(S)-Benzyl 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)pyrr...;(S)-benzyl 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)pyrrolidine;(S)-benzyl 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate;benzyl (S)-2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate;benzyl (2S)-2-{8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl}pyrrolidine-1-carboxylate;(S)-benzyl 2-(8-amino-1-bromoimidazo[1,5-a]pyrazine-3-yl)pyrrolidine-1-carboxylate
CBNumber:
CB53062794
Molecular Formula:
C18H18BrN5O2
Molecular Weight:
416.27
MOL File:
1420478-88-1.mol
MSDS File:
SDS
Modify Date:
2024/6/3 16:17:09

(2S)-2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1-Pyrrolidinecarboxylic acid phenylmethyl ester Properties

Density 1?+-.0.1 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
pka 4.67±0.30(Predicted)
InChI InChI=1S/C18H18BrN5O2/c19-15-14-16(20)21-8-10-24(14)17(22-15)13-7-4-9-23(13)18(25)26-11-12-5-2-1-3-6-12/h1-3,5-6,8,10,13H,4,7,9,11H2,(H2,20,21)/t13-/m0/s1
InChIKey DLXYYJDQLZHBNU-ZDUSSCGKSA-N
SMILES N1(C(OCC2=CC=CC=C2)=O)CCC[C@H]1C1N2C=CN=C(N)C2=C(Br)N=1

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338

(2S)-2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1-Pyrrolidinecarboxylic acid phenylmethyl ester Chemical Properties,Uses,Production

Uses

(2S)-2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1-Pyrrolidinecarboxylic acid phenylmethyl ester is used to Acalabrutinib intermediate.

Synthesis

Synthesis_1420478-88-1
Compound 4b (46.33 g, 100 mmol) and toluene (463 mL) were added to a three-neck flask.After stirring uniformly, trifluoroacetic acid (18.02 g, 300 mmol) was slowly added.Heat to 75-80 ?? C for 6-8 hours.The raw materials disappeared and then cooled to room temperature.Wash with 5% sodium hydroxide solution (463 mL).Washed once with saturated saline (231 mL),Dry over sodium sulfate, filter,The filtrate was added with ammonium acetate (38.54 g, 500 mmol).Heating and refluxing for 10 to 16 hours,The reaction was cooled to room temperature.Add water (463 mL),Dispensing after stirring,The aqueous phase was extracted once more with toluene,The combined organic phases were washed with saturated brine (231 mL).Dry with sodium sulfate,Concentrated to remove the solvent,Isopropanol petroleum ether mixed solvent recrystallized,Filter, dryCompound 6b (31.64 g, 2 steps 76%) was dried.

(2S)-2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1-Pyrrolidinecarboxylic acid phenylmethyl ester Preparation Products And Raw materials

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(2S)-2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1-Pyrrolidinecarboxylic acid phenylmethyl ester Spectrum

1-Pyrrolidinecarboxylic acid, 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-, phenylmethyl ester, (2S)- benzyl (S)-2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate (S)-benzyl 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate benzyl (2S)-2-{8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl}pyrrolidine-1-carboxylate S)-2-(8-Amino-1-bromo-imidazo[1,5-a]pyrazin-3-yl)-pyrrolidine -1-carboxylic acid benzyl ester (2S)-2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1-Pyrrolidinecarboxylic acid phenylmethyl ester ACP-196-1 EOS-60755 1-Pyrrolidinecarboxylic acid, 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-, phenylmethyl ester, Acalabrutinib Intermediate 1 (S)-Benzyl 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin (S)-benzyl 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)pyrrolidine (S)-Benzyl 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)pyrr... Phenylmethyl (2S)-2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1-pyrrolidinecarboxylate (S)-benzyl 2-(8-amino-1-bromoimidazo[1,5-a]pyrazine-3-yl)pyrrolidine-1-carboxylate 1420478-88-1 142078-88-1