Hydrogen chloride-ethyl acetate → 6-fluoro-1-(4-methoxybutyl)-N-(2-methylpropyl)-N-[(3S,5R)-5-(morpholin-4-ylcarbonyl)piperidin-3-yl]-1H-benzimidazole-2-carboxamide dihydrochloride

HRID 1509417Notes

Reaction equation

HRID 1509417 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]([N:12]([CH2:34][CH:35]([CH3:37])[CH3:36])[C@H:13]3[CH2:18][C@@H:17]([C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[O:20])[CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]3)=[O:11])[N:7]([CH2:38][CH2:39][CH2:40][CH2:41][O:42][CH3:43])[C:6]=2[CH:44]=1.C(OCC)(=O)C.[ClH:51]>>[ClH:51].[ClH:51].[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]([N:12]([CH2:34][CH:35]([CH3:37])[CH3:36])[C@H:13]3[CH2:18][C@@H:17]([C:19]([N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)=[O:20])[CH2:16][NH:15][CH2:14]3)=[O:11])[N:7]([CH2:38][CH2:39][CH2:40][CH2:41][O:42][CH3:43])[C:6]=2[CH:44]=1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 58355258tert-butyl (3S,5R)-3-[{[6-fluoro-1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate

Product 1

HCID 673210346-fluoro-1-(4-methoxybutyl)-N-(2-methylpropyl)-N-[(3S,5R)-5-(morpholin-4-ylcarbonyl)piperidin-3-yl]-1H-benzimidazole-2-carboxamide dihydrochloride

Procedure

tert-Butyl (3S,5R)-3-[{[6-fluoro-1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate was dissolved in 4M hydrogen chloride-ethyl acetate (5 ml), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was concentrated to give the object product (567 mg).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-acb9d00261654244ad6a96b5a36b3102
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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