Dimethylamine → 5-[3-{[(2,2-dimethylpropyl)amino]methyl}-4,5-bis(methyloxy)phenyl]-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

HRID 562079Notes

Reaction equation

C[N:2]([CH2:4][C:5]1[CH:6]=[C:7]([C:15]2[CH:16]=[C:17]3[C:21](=[C:22]([C:24]([NH2:26])=[O:25])[CH:23]=2)[NH:20][CH:19]=[C:18]3[CH:27]2[CH2:32][CH2:31][N:30]([S:33]([CH2:36][CH3:37])(=[O:35])=[O:34])[CH2:29][CH2:28]2)[CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH3:3].CNC>>[CH3:4][C:5]([CH3:6])([CH3:10])[CH2:3][NH:2][CH2:4][C:5]1[CH:6]=[C:7]([C:15]2[CH:16]=[C:17]3[C:21](=[C:22]([C:24]([NH2:26])=[O:25])[CH:23]=2)[NH:20][CH:19]=[C:18]3[CH:27]2[CH2:28][CH2:29][N:30]([S:33]([CH2:36][CH3:37])(=[O:35])=[O:34])[CH2:31][CH2:32]2)[CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12]

Participants

Reactant 2

HCID 674Dimethylamine

HCID 160373075-[3-[(dimethylamino)methyl]-4,5-bis(methyloxy)phenyl]-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

Product 1

HCID 160373105-[3-{[(2,2-dimethylpropyl)amino]methyl}-4,5-bis(methyloxy)phenyl]-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamideYield 29.2%

Procedure

The title compound was prepared according to the general procedure of 5-[3-[(dimethylamino)methyl]-4,5-bis(methyloxy)phenyl]-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide, substituting (2,2-dimethylpropyl)amine (20 μL, 0.30 mmol) for dimethylamine to afford 10 mg of the title compound (29.2%).

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-451181feaed8400a83064a896c994f58
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063071B2

Reaction notes

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