N-(6-acetyl-2-chloro-3-methoxyphenyl)-4-cyclopropylthiazole-2-carboxamide → N-(6-Acetyl-2-chloro-3-methoxyphenyl)-4-cyclobutylthiazole-2-carboxamide

HRID 880792Notes

Reaction equation

HRID 880792 reaction equation
[CH:1]1([C:5]2[N:6]=[C:7]([C:10](Cl)=[O:11])[S:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:13]([C:16]1[C:21]([NH:22]C(C2SC=C(C3CC3)N=2)=O)=[C:20]([Cl:33])[C:19]([O:34][CH3:35])=[CH:18][CH:17]=1)(=[O:15])[CH3:14]>>[C:13]([C:16]1[C:21]([NH:22][C:10]([C:7]2[S:8][CH:9]=[C:5]([CH:1]3[CH2:4][CH2:3][CH2:2]3)[N:6]=2)=[O:11])=[C:20]([Cl:33])[C:19]([O:34][CH3:35])=[CH:18][CH:17]=1)(=[O:15])[CH3:14]

Participants

3

Reactant 2

HCID 59434816N-(6-acetyl-2-chloro-3-methoxyphenyl)-4-cyclopropylthiazole-2-carboxamideHCID 866464084-Cyclobutylthiazole-2-carbonyl chloride

Product 1

HCID 66730303N-(6-Acetyl-2-chloro-3-methoxyphenyl)-4-cyclobutylthiazole-2-carboxamideYield 70%

Procedure

N-(6-Acetyl-2-chloro-3-methoxyphenyl)-4-cyclobutylthiazole-2-carboxamide 268b was synthesized from compound 267b (5.48 g, 1.2 eq.) as a white solid in 70% yield, following the procedure as described for compound 268a. 1H NMR (CDCl3, 400 MHz): δ (ppm) 1.96-2.12 (m, 2H), 2.34-2.44 (m, 4H), 2.59 (s, 3H), 3.70-3.78 (m, 1H), 3.99 (s, 3H), 6.88 (d, J=8.82 Hz, 1H), 7.20 (s, 1H), 7.68 (d, J=8.76 Hz, 1H), 10.33 (br s, 1H); MS (ESI, EI−): m/z=365 (MH+).

Sources & evidence

ORD record
ord-c0b1f7d3a61f4cebad7ded11eecda529
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

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