2-Methyl-3-phenylprop-2-enoic acid → N-[2-(3-Dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-yl]-2-methyl-3-phenyl-acrylamide

HRID 1174902Notes

Reaction equation

HRID 1174902 reaction equation
[CH3:1][C:2](=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=O.[CH3:13][N:14]([CH3:30])[CH:15]1[CH2:19][CH2:18][N:17]([C:20]2[S:21][C:22]3[CH:28]=[C:27]([NH2:29])[CH:26]=[CH:25][C:23]=3[N:24]=2)[CH2:16]1>>[CH3:13][N:14]([CH3:30])[CH:15]1[CH2:19][CH2:18][N:17]([C:20]2[S:21][C:22]3[CH:28]=[C:27]([NH:29][C:3](=[O:5])[C:2]([CH3:1])=[CH:6][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)[CH:26]=[CH:25][C:23]=3[N:24]=2)[CH2:16]1

Participants

3

Reactant 2

HCID 145412-Methyl-3-phenylprop-2-enoic acidHCID 632315072-(3-Dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamine

Product 1

HCID 68773887N-[2-(3-Dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-yl]-2-methyl-3-phenyl-acrylamideYield 12.5%

Procedure

Prepare according to Method B, using α-methylcinnamic acid (99 mg, 0.610 mmol) and 2-(3-dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamine (162 mg, 0.618 mmol) to yield the title compound (31 mg, 12%). mass spectrum (m/e): 407.3 [M+H], 405.2 [M−H].

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-b7b09b6319774ceb8e77367715c08e81
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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