ChemicalBook CAS DataBase List S-1-Pyrrolidinecarboxylic acid, 2-(6-bromo-1H-benzimidazol-2-yl)-, 1,1-dimethyleth

S-1-Pyrrolidinecarboxylic acid, 2-(6-bromo-1H-benzimidazol-2-yl)-, 1,1-dimethyleth synthesis

8synthesis methods

Product Name:S-1-Pyrrolidinecarboxylic acid, 2-(6-bromo-1H-benzimidazol-2-yl)-, 1,1-dimethyleth
CAS Number:1208007-67-3
Molecular formula:C16H20BrN3O2
Molecular Weight:366.25

15761-39-4
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$5.00/10g

1575-37-7
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S-1-Pyrrolidinecarboxylic acid, 2-(6-bromo-1H-benzimidazol-2-yl)-, 1,1-dimethyleth

1208007-67-3
31 suppliers
$1050.00/5G

Yield:1208007-67-3 81%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine;HATU in tetrahydrofuran at 0 - 20; for 4.5 h;

Steps:

1.9 Step 9) the preparation of compound 1-11

To a solution of compound 1-10 (20 g. 107 mmol) and compound HATU (48.82 g. 128.4 mmol) in THF (250 mL) was added DIPEA (19.5 mL, 118 mmol) at 0 °C. After stirring at 0 °C for 0.5 hr. to the solution was added the compound 1 -10-2 (25.6 g, 119 mmol) in a portionwise manner, then the reaction mixture was stirred at rt for 4 hrs. After the reaction was completed, the reaction was quenched with water (100 mL), the solvent THF was removed, and the resulting mixture was extracted with EtOAc (200 mL x 3). The combined organic layers were dried over anhydrous Na₂S0₄ and concentrated in vacuo. The residue was dissolved in glacial acetic acid (100 mL). The solution was stirred at 40 °C overnight, and HOAc was removed. The resulting mixture was dissolved in EtOAc (400 mL), washed with Na₂C0₃ aq (150 mL x 3) and dried over anhydrous Na₂S0₄ and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 1/2) to give the title compound (35 g, 81 %). The compound was characterized by the following spectroscopic data: MS (ESI, pos.ion) mlz: 367.3 [M+H] ⁺; NMR (400 MHz, CDC1₃) 0 (ppm): 7.68 (s, 1 H), 7.42-7.40 (m, 1 H), 7.30-7.28 (m. 1 H), 5.11 -5.09 (m. 1 H), 3.45-3.43 (m. 2H). 2.94-2.93 (m. 1 H), 2.21-2.18 (m, 2H). 2.01 -1.91 (m, 1 H), 1 .49 (s, 9H).

References:

WO2014/19344,2014,A1 Location in patent:Paragraph 00335