Oxalyl chloride → 3-(3,4-Difluoro-phenyl)-N-[2-(3-dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-yl]-acrylamide

HRID 1174901Notes

Reaction equation

HRID 1174901 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[F:13])[CH:5]=[CH:6][C:7]([OH:9])=O.C(Cl)(=O)C(Cl)=O.[CH3:20][N:21]([CH3:37])[CH:22]1[CH2:26][CH2:25][N:24]([C:27]2[S:28][C:29]3[CH:35]=[C:34]([NH2:36])[CH:33]=[CH:32][C:30]=3[N:31]=2)[CH2:23]1>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]([NH:36][C:34]2[CH:33]=[CH:32][C:30]3[N:31]=[C:27]([N:24]4[CH2:25][CH2:26][CH:22]([N:21]([CH3:37])[CH3:20])[CH2:23]4)[S:28][C:29]=3[CH:35]=2)=[O:9])[CH:10]=[CH:11][C:12]=1[F:13]

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 1454863-(3,4-Difluorophenyl)prop-2-enoic acidHCID 632315072-(3-Dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamine

Product 1

HCID 687698513-(3,4-Difluoro-phenyl)-N-[2-(3-dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-yl]-acrylamideYield 77%

Procedure

Prepare according to Method C (Example 9), using 3,4-difluorocinnamic acid (107 mg, 0.581 mmol), oxalyl chloride (250 μL, 2.87 mmol), and 2-(3-dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamine (100 mg, 0.382 mmol) to afford the title compound (126 mg, 77%). mass spectrum (m/e): 429.0 [M+H], 427.0 [M−H]. 1H NMR (400 MHz, DMSO-d6) δ 10.23 (s, 1H), 8.25 (d, 1H, J=0.9 Hz), 7.72 (m, 1H), 7.55 (d, 1H, J=15.3 Hz), 7.52-7.48 (m, 2H), 7.43-7.41 (m, 2H), 6.80 (d, 1H, J=15.8 Hz), 3.70 (dd, 1H, J=9.7, 7.0 Hz), 3.61 (m, 1H), 3.47 (m, 1H), 3.26 (dd, 1H, J=9.9, 8.1 Hz), 2.88 (m, 1H), 2.21-2.17 (m, 7H), 1.90 (m, 1H).

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-1a5ac393964e495f85bbc96b68d8e785
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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