HCID 13737222, compound → HCID 57991640, compound

HRID 556106Notes

Reaction equation

HRID 556106 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.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH2:32][CH2:33][C:34](Cl)=[O:35])[CH:27]=[CH:28][C:29]=1[O:30][CH3:31]>>[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:34](=[O:35])[CH2:33][CH2:32][C:26]2[CH:27]=[CH:28][C:29]([O:30][CH3:31])=[C:24]([O:23][CH3:22])[CH:25]=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 13737222HCID 13737222, compoundHCID 156207023-(3,4-Dimethoxyphenyl)propionyl chloride

Product 1

HCID 57991640HCID 57991640, compoundYield 65%

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-(3,4-dimethoxy-phenyl)-propionyl chloride prepared in the step 1 were used as starting materials, allowed to react at 35-40° C. for 10 hours, followed by post-treatment to obtain a crude product, which was purified by a silica gel column chromatography eluted with petroleum ether and ethyl acetate (4:1) to obtain a product as a white solid in a yield of 65.0%, mp: 142-143└. 1H-NMR (CDCl3, 400 MHz) δ: 2.12 (2H, t, J=7.72 Hz), 2.74 (2H, t, J=7.72 Hz), 3.80 (6H, s, 2×OCH3), 3.83 (3H, s, OCH3), 4.18 (2H, s, CH2), 6.51 (1H, dd, J=8.16, 1.96 Hz, ArH), 6.56 (1H, d, J=1.96 Hz, ArH), 6.69 (1H, d, J=8.16 Hz, ArH), 6.83 (2H, d, J=8.68 Hz, ArH), 7.21˜7.33 (5H, m, ArH), 7.42 (2H, d, J=8.68 Hz, ArH), 11.05 (1H, br, CONH); EI-MS m/e (%): 488.1 (M+, 66), 296.0 (100); HREI-MS Calcd. for C28H28N2O4S: 488.1770. found: 488.1764. Anal. Calcd. for C28H28N2O4S: C, 68.83; H, 5.78; N, 5.73. found: C, 68.69; H, 5.67; N, 6.09.

Workup

  1. customto react at 35-40° C. for 10 hours
  2. customto obtain a crude product, which
  3. customwas purified by a silica gel column chromatography
  4. washeluted with petroleum ether and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-68b649457bd64a19a37b1394cdacb7f7
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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