CHIR-090 synthesis
- Product Name:CHIR-090
- CAS Number:728865-23-4
- Molecular formula:C24H27N3O5
- Molecular Weight:437.49
![Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-](/CAS/20210305/GIF/1000210-73-0.gif)
1000210-73-0
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728865-23-4
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Yield: 81%
Reaction Conditions:
with hydroxylamine hydrochloride;sodium methylate in tetrahydrofuran;methanol at 0 - 20; for 5 h;Inert atmosphere;
Steps:
15 Preparation of (2S, 3R)-N-(2-Hydroxy-1-hydroxycarbamoyl-propyl)-4-(4-morpholin-4-ylmethyl-phenylethynyl)-benzamide (5).
Sodium methoxide (25 wt% in MeOH, 1.860 g, 8.60 mmol) was added to a stirred solution of hydroxylaminehydrochloride (400 mg, 5.76 mmol) in anhydrous MeOH (5 mL) at 0 °C under N2 atmosphere. After stirring 20 min, asolution of methyl ester 4 (829 mg, 1.90 mmol) in 1:1 MeOH/THF (6 mL) was added and the reaction mixture stirred at0 °C for 1 h and at room temperature for 4 h. The reaction was quenched with 1.0 M HCl (6 mL), concentrated by rotaryevaporation to remove organic solvents, and diluted with DMSO (4 mL). Analytical RP-HPLC (C18 column, CH3CNgradient 5-35%, 0.1% TFA, UV analysis 300 nm, 16 min) indicated a purity of 85% for the crude product mixture.Purification by preparative RP-HPLC and lyophilization of the collected fractions gave 701 mg (81%) of 5 as a fluffywhite solid. LRMS (ES+) m/z 438.1 (C24H27N3O5 + H requires 438.20); RP-HPLC (300 nm,16 min run) 8.7 min.
References:
The University of Washington;Novartis Vaccines and Diagnostics, Inc.;Andersen, Niels H.;Bowman, Jason;Erwin, Alice;Harwood, Eric;Kline, Toni;Mdluli, Khisimuzi;Ng, Simon;Pfister, Keith B.;Shawar, Ribhi;Wagman, Allan;Yabannavar, Asha EP2295402, 2015, B1 Location in patent:Paragraph 0221; 0222
110-91-8
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1000210-73-0
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728865-23-4
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$45.00/1mg
1000210-73-0
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728865-23-4
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15164-44-0
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728865-23-4
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1000210-73-0
0 suppliers
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728865-23-4
85 suppliers
$45.00/1mg