(2E)-3-(3-Fluorophenyl)-2-propenoic acid → N-[2-(3-Dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-yl]-3-(3-fluoro-phenyl)-acrylamide

HRID 1174898Notes

Reaction equation

HRID 1174898 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7]([OH:9])=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:7](=[O:9])[CH:6]=[CH:5][C:4]4[CH:10]=[CH:11][CH:12]=[C:2]([F:1])[CH:3]=4)[CH:26]=[CH:25][C:23]=3[N:24]=2)[CH2:16]1

Participants

3

Reactant 2

HCID 1551219(2E)-3-(3-Fluorophenyl)-2-propenoic acidHCID 632315072-(3-Dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamine

Product 1

HCID 68771353N-[2-(3-Dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-yl]-3-(3-fluoro-phenyl)-acrylamideYield 16.9%

Procedure

Prepare according to Method B, using trans-3-fluorocinnamic acid (98 mg, 0.590 mmol) and 2-(3-dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamine (162 mg, 0.618 mmol) to afford the title compound (41 mg, 16%). mass spectrum (m/e): 411.2 [M+H], 409.2 [M−H].

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-26c3186225c64975bb66f85578b8dfef
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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