Methanamine, hydrochloride (1:1) → 1-{1-[(4-Fluorophenyl)sulfonyl]-5-[2-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl}-N-methylmethanamine hydrochloride

HRID 554396Notes

Reaction equation

HRID 554396 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])=[CH:14][C:13]([CH:26]=O)=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl-:28].C[NH3+].[C:31]([BH3-])#[N:32].[Na+]>>[ClH:28].[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])=[CH:14][C:13]([CH2:26][NH:32][CH3:31])=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 11637Methanamine, hydrochloride (1:1)HCID 5003444Sodium cyanoborohydrideHCID 866207401-[(4-Fluorophenyl)sulfonyl]-5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carbaldehyde

Product 1

HCID 669253021-{1-[(4-Fluorophenyl)sulfonyl]-5-[2-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl}-N-methylmethanamine hydrochlorideYield 53.1%

Procedure

Using 1-[(4-fluorophenyl)sulfonyl]-5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carbaldehyde (0.55 g), methylammonium chloride (1.17 g) and sodium cyanoborohydride (0.27 g), a procedure as in Example 4 was performed to give the title compound as a colorless crystal (yield 0.33 g, 53%).

Sources & evidence

ORD record
ord-14d2bcb13dea4207a4d02c822d93dd90
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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