Cinnamic Acid → N-[2-(3-Dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-yl]-3-phenyl-acrylamide

HRID 1174897Notes

Reaction equation

HRID 1174897 reaction equation
[C:1]([OH:11])(=O)/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:12][N:13]([CH3:29])[CH:14]1[CH2:18][CH2:17][N:16]([C:19]2[S:20][C:21]3[CH:27]=[C:26]([NH2:28])[CH:25]=[CH:24][C:22]=3[N:23]=2)[CH2:15]1>>[CH3:12][N:13]([CH3:29])[CH:14]1[CH2:18][CH2:17][N:16]([C:19]2[S:20][C:21]3[CH:27]=[C:26]([NH:28][C:1](=[O:11])[CH:2]=[CH:3][C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:25]=[CH:24][C:22]=3[N:23]=2)[CH2:15]1

Participants

3

Reactant 2

HCID 444539Cinnamic AcidHCID 632315072-(3-Dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamine

Product 1

HCID 68772081N-[2-(3-Dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-yl]-3-phenyl-acrylamideYield 13%

Procedure

Prepare according to Method B, using trans-cinnamic acid (96 mg, 0.648 mmol) and 2-(3-dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamine (162 mg, 0.618 mmol) to afford the title compound (31 mg, 13%). mass spectrum (m/e): 393.0 [M+H]. 1H NMR (400 MHz, DMSO-d6): δ 10.21 (s, 1H), 8.26 (d, 1H, J=1.3 Hz), 7.63 (d, 2H, J=7.0 Hz), 7.57 (d, 1H, J=15.7 Hz), 7.48-7.37 (m, 5H), 6.84 (d, 1H, J=15.8 Hz), 3.70 (dd, 1H, J =9.5, 7.0 Hz), 3.61 (m, 1H), 3.46 (m, 1H), 3.27 (m, 1H), 2.88 (m, 1H), 2.23-2.11 (m, 7H), 1.90 (m, 1H).

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-1611741dce774b418b5e66ce6f19ec84
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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