Veratroyl chloride → HCID 86636629, compound

HRID 556061Notes

Reaction equation

HRID 556061 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[S:11][C:10]([NH2:12])=[N:9][C:8]=2[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[C:28](Cl)=[O:29]>>[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[S:11][C:10]([NH:12][C:28](=[O:29])[C:27]3[CH:31]=[CH:32][C:33]([O:34][CH3:35])=[C:25]([O:24][CH3:23])[CH:26]=3)=[N:9][C:8]=2[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 77070Veratroyl chlorideHCID 57991595HCID 57991595, compound

Product 1

HCID 86636629HCID 86636629, compoundYield 69.1%

Procedure

A procedure similar to that in Example 4 was used. 5-(4-fluoro-benzyl)-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 21 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 obtain a crude product, which was purified by a silica gel column chromatography eluted with a gradient of dichloromethane and ethyl acetate (100:0-10:1) to obtain a product as a white solid in a yield of 69.1%, mp: 140-142 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.80 (3H, s, OCH3), 3.84 (3H, s, OCH3), 3.91 (3H, s, OCH3), 4.18 (2H, s, CH2), 6.79 (1H, d, J=8.68 Hz, ArH), 6.82 (2H, d, J=8.68 Hz, ArH), 7.00 (2H, t, 3JFH=3JHH=8.68 Hz, ArH), 7.21 (2H, dd, 3JHH=8.12 Hz, 4JFH=5.32 Hz, ArH), 7.35 (4H, d, J=9.28 Hz, ArH), 11.00 (1H, br, CONH, exchangable); EI-MS m/e (%): 478.2 (M+, 88), 165.0 (100); HREI-MS Calcd. for C26H23FN2O4S: 478.1363. found: 478.1361. Anal. Calcd. for C26H23FN2O4S: C, 65.26; H, 4.84; N, 5.85. found: C, 65.11; H, 4.68; N, 5.96.

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 (100:0-10:1)

Sources & evidence

ORD record
ord-4cf2922f8c074f4f8b2c0f33ed92d720
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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