Veratroyl chloride → N-[5-cyclohexylmethyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3,4-dimethoxy-benzamide

HRID 556081Notes

Reaction equation

HRID 556081 reaction equation
[CH:1]1([CH2:7][C:8]2[S:12][C:11]([NH2:13])=[N:10][C:9]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[C:27](Cl)=[O:28]>>[CH:1]1([CH2:7][C:8]2[S:12][C:11]([NH:13][C:27](=[O:28])[C:26]3[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:24]([O:23][CH3:22])[CH:25]=3)=[N:10][C:9]=2[C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 77070Veratroyl chlorideHCID 579916265-Cyclohexylmethyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine

Product 1

HCID 57991617N-[5-cyclohexylmethyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3,4-dimethoxy-benzamideYield 67.5%

Procedure

A procedure similar to that in Example 4 was used. 5-cyclohexylmethyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 47 and 3,4-dimethoxy-benzoyl chloride prepared in the step 1 of Example 12 were used as starting materials, allowed to react at room temperature overnight, followed by post-treatment to give a crude product, which was purified by a silica gel column chromatography eluted with a gradient of dichloromethane and ethyl acetate (20:1) to obtain a product as a white solid in a yield of 67.5%, mp: 171-172 └. 1H-NMR (CDCl3, 400 MHz) δ: 0.82˜0.98 (2H, m), 1.08˜1.28 (3H, m), 1.58˜1.88 (6H, m), 2.74 (2H, d, J=7.28 Hz, CHCH2Ar), 3.82 (3H, s, OCH3), 3.89 (3H, s, OCH3), 3.94 (3H, s, OCH3), 6.82˜6.89 (3H, m, ArH), 7.35˜7.47 (4H, m, ArH), 11.00 (1H, br, CONH); EI-MS m/e (%): 466.2 (M+, 46), 383.2 (29), 165.1 (100); HREI-MS Calcd. for C26H30N2O4S: 466.1926. found: 466.1920. Anal. Calcd. for C26H30N2O4S: C, 66.93; H, 6.48; N, 6.00. found: C, 66.88; H, 6.68; N, 6.02.

Workup

  1. customto react at room temperature overnight
  2. customto give 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)

Sources & evidence

ORD record
ord-fd498e058eb34539a110122b5e384bb6
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

Loading…