Benzoyl chloride, 3,4,5-trimethoxy- → N-[5-cyclohexylmethyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3,4,5-trimethoxy-benzamide

HRID 556083Notes

Reaction equation

HRID 556083 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]C)=[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]=[C:31]([O:35][CH3:36])[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:25]=[C:24]([O:23][CH3:22])[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=3)=[N:10][C:9]=2[C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 579916265-Cyclohexylmethyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine

Product 1

HCID 86636632N-[5-cyclohexylmethyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3,4,5-trimethoxy-benzamideYield 60.1%

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 3,4,5-trimethoxy-benzoyl chloride prepared in the step 1 of Example 37 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 60.1%, mp: 193-194└. 1H-NMR (CDCl3, 400 MHz) δ: 0.85˜0.98 (2H, m), 1.05˜1.28 (3H, m), 1.58˜1.88 (6H, m), 2.75 (2H, d, J=7.28 Hz, CHCH2Ar), 3.74 (3H, s, OCH3), 3.77 (3H, s, OCH3), 3.79 (3H, s, OCH3), 3.97 (3H, s, OCH3), 6.77 (2H, d, J=8.44 Hz, ArH), 6.98 (2H, s, ArH), 7.29 (2H, d, J=8.44 Hz, ArH); EI-MS m/e (%): 496.1 (M+, 64), 413.1 (48), 195.1 (100); HREI-MS Calcd. for C27H32N2O5S: 496.2032. found: 496.2040. Anal. Calcd. for C27H32N2O5S: C, 65.30; H, 6.49; N, 5.64. found: C, 65.11; H, 6.55; N, 5.70.

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-f490008a1e2e437397ec9ceb01d730b3
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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