Methanamine, hydrochloride (1:1) → N-Methyl-1-{5-(3-fluorophenyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-3-yl}methanamine hydrochloride

HRID 554390Notes

Reaction equation

HRID 554390 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:11]=[C:10]([CH:23]=O)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Cl-:25].C[NH3+].[C:28]([BH3-])#[N:29].[Na+]>>[ClH:25].[CH3:28][NH:29][CH2:23][C:10]1[CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[N:12]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:11]=1

Participants

4

Reactant 3

HCID 11637Methanamine, hydrochloride (1:1)HCID 5003444Sodium cyanoborohydrideHCID 866207745-(3-fluorophenyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrrole-3-carbaldehyde

Product 1

HCID 66924776N-Methyl-1-{5-(3-fluorophenyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-3-yl}methanamine hydrochlorideYield 69%

Procedure

Using 5-(3-fluorophenyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrrole-3-carbaldehyde (0.57 g), methylammonium chloride (1.38 g) and sodium cyanoborohydride (0.32 g), a procedure as in Example 4 was performed to give the title compound as white crystals (yield 0.45 g, 69%).

Sources & evidence

ORD record
ord-05c8986e4e1942aba52aa224b8be9d61
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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