3,5-Difluorobenzoyl chloride → N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3,5-difluoro-benzamide

HRID 556049Notes

Reaction equation

HRID 556049 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([NH2:13])=[N:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:22][C:23]1[CH:24]=[C:25]([CH:29]=[C:30]([F:32])[CH:31]=1)[C:26](Cl)=[O:27]>>[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:26](=[O:27])[C:25]2[CH:24]=[C:23]([F:22])[CH:31]=[C:30]([F:32])[CH:29]=2)=[N:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 1456003,5-Difluorobenzoyl chlorideHCID 137372225-Benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine

Product 1

HCID 57991598N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3,5-difluoro-benzamideYield 59.1%

Procedure

A procedure similar to that in Example 4 was used. 5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 1 and 3,5-difluorobenzoyl chloride prepared in the step 1 were used as starting materials, allowed to react at room temperature overnight, followed by post-treatment to obtain a crude product, which was purified by a silica gel column chromatography eluted with a gradient of dichloromethane and ethyl acetate (20:1-10:1) to obtain a product as a white solid in a yield of 59.1%, mp: 154-155└. 1H-NMR (CDCl3, 400 MHz) δ: 3.77 (3H, s, OCH3), 4.23 (2H, s, CH2), 6.72 (2H, d, J=8.44 Hz, ArH), 6.82 (1H, t, 3JFH=8.40 Hz, ArH), 7.17˜7.37 (9H, m, ArH), 11.97 (1H, br, CONH); EI-MS m/e (%): 436.1 (M+, 100), 141.0 (36); HREI-MS Calcd. for C24H18F2N2O2S: 436.1057. found: 436.1053. Anal. Calcd. for C24H18F2N2O2S: C, 66.04; H, 4.16; N, 6.42. found: C, 66.02; H, 4.08; N, 6.44.

Workup

  1. customto react at room temperature overnight
  2. customto obtain a crude product, which
  3. customwas purified by a silica gel column chromatography
  4. washeluted with a gradient of dichloromethane and ethyl acetate (20:1-10:1)

Sources & evidence

ORD record
ord-9836be2008cf4b86ae27795cb750774b
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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