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S-1-Pyrrolidinecarboxylic acid, 2-(6-bromo-1H-benzimidazol-2-yl)-, 1,1-dimethyleth synthesis
- 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
![BOC-L-Proline](/CAS/20180808/GIF/15761-39-4.gif)
15761-39-4
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![4-Bromo-1,2-benzenediamine](/CAS/GIF/1575-37-7.gif)
1575-37-7
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![S-1-Pyrrolidinecarboxylic acid, 2-(6-bromo-1H-benzimidazol-2-yl)-, 1,1-dimethyleth](/CAS/20150408/GIF/1208007-67-3.gif)
1208007-67-3
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$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
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![S-1-Pyrrolidinecarboxylic acid, 2-(6-bromo-1H-benzimidazol-2-yl)-, 1,1-dimethyleth](/CAS/20150408/GIF/1208007-67-3.gif)
1208007-67-3
32 suppliers
$1050.00/5G
![N-BOC-L-Prolinal](/CAS/GIF/69610-41-9.gif)
69610-41-9
250 suppliers
$9.00/1g
![4-Bromo-1,2-benzenediamine](/CAS/GIF/1575-37-7.gif)
1575-37-7
367 suppliers
$10.00/1g
![S-1-Pyrrolidinecarboxylic acid, 2-(6-bromo-1H-benzimidazol-2-yl)-, 1,1-dimethyleth](/CAS/20150408/GIF/1208007-67-3.gif)
1208007-67-3
32 suppliers
$1050.00/5G
![BOC-L-Proline](/CAS/20180808/GIF/15761-39-4.gif)
15761-39-4
603 suppliers
$5.00/10g
![S-1-Pyrrolidinecarboxylic acid, 2-(6-bromo-1H-benzimidazol-2-yl)-, 1,1-dimethyleth](/CAS/20150408/GIF/1208007-67-3.gif)
1208007-67-3
32 suppliers
$1050.00/5G
![4-Bromo-1,2-benzenediamine](/CAS/GIF/1575-37-7.gif)
1575-37-7
367 suppliers
$10.00/1g
![S-1-Pyrrolidinecarboxylic acid, 2-(6-bromo-1H-benzimidazol-2-yl)-, 1,1-dimethyleth](/CAS/20150408/GIF/1208007-67-3.gif)
1208007-67-3
32 suppliers
$1050.00/5G