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

HRID 1509444Notes

Reaction equation

HRID 1509444 reaction equation
[C:1]([C@@H:4]1[CH2:9][C@H:8]([N:10]([C:15]([C:17]2[N:21]([CH2:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])[C:20]3[CH:28]=[CH:29][CH:30]=[CH:31][C:19]=3[N:18]=2)=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1)(=[O:3])[NH2:2].C(OCC)(=O)C.[ClH:45]>C(OCC)(=O)C>[ClH:45].[ClH:45].[C:1]([C@H:4]1[CH2:5][NH:6][CH2:7][C@@H:8]([N:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:15]([C:17]2[N:21]([CH2:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])[C:20]3[CH:28]=[CH:29][CH:30]=[CH:31][C:19]=3[N:18]=2)=[O:16])[CH2:9]1)(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 58355659tert-Butyl (3R,5S)-3-carbamoyl-5-{{{1-(4-methoxybutyl)-1H-benzimidazol-2-yl}carbonyl}(2-methylpropyl)amino}piperidine-1-carboxylate

Product 1

HCID 67320977N-[(3S,5R)-5-carbamoylpiperidin-3-yl]-1-(4-methoxybutyl)-N-(2-methylpropyl)-1H-benzimidazole-2-carboxamide dihydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl (3R,5S)-3-carbamoyl-5-[{[1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-1-carboxylate (260 mg) was dissolved in ethyl acetate (3 ml), 4N hydrogen chloride-ethyl acetate (5 ml) was added, and the mixture was stirred for 1 hr. The solvent was evaporated under reduced pressure to give the object product (220 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e11837475aa04e10995e24c820128bfa
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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