Hydrochloride methanol → 6-fluoro-N-[(3S,5R)-5-(hydroxymethyl)piperidin-3-yl]-1-(4-methoxybutyl)-N-(2-methylpropyl)-1H-benzimidazole-2-carboxamide dihydrochloride

HRID 2168913Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]([N:12]([CH2:28][CH:29]([CH3:31])[CH3:30])[C@H:13]3[CH2:18][C@@H:17]([CH2:19][OH:20])[CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]3)=[O:11])[N:7]([CH2:32][CH2:33][CH2:34][CH2:35][O:36][CH3:37])[C:6]=2[CH:38]=1.[ClH:39].CO>>[ClH:39].[ClH:39].[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]([N:12]([C@H:13]3[CH2:18][C@@H:17]([CH2:19][OH:20])[CH2:16][NH:15][CH2:14]3)[CH2:28][CH:29]([CH3:31])[CH3:30])=[O:11])[N:7]([CH2:32][CH2:33][CH2:34][CH2:35][O:36][CH3:37])[C:6]=2[CH:38]=1

Participants

Reactant 2

HCID 21893726Hydrochloride methanol

HCID 58355683tert-butyl (3S,5R)-3-[{[6-fluoro-1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]-5-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 673212246-fluoro-N-[(3S,5R)-5-(hydroxymethyl)piperidin-3-yl]-1-(4-methoxybutyl)-N-(2-methylpropyl)-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-(hydroxymethyl)piperidine-1-carboxylate (182 mg) was dissolved in 10-20% hydrogen chloride-methanol (5 ml), and the mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated to give the object product (169 mg).

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-b32a4ca6dbd64b24b792a3fa07261cd7
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045436B2

Reaction notes

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