N-(6-Acetyl-2-chloro-3-methoxyphenyl)-4-cyclobutylthiazole-2-carboxamide → HCID 178487690, compound

HRID 388697Notes

Reaction equation

HRID 388697 reaction equation
[C:1]([C:4]1[C:9]([NH:10][C:11]([C:13]2[S:14][CH:15]=[C:16]([CH:18]3[CH2:21][CH2:20][CH2:19]3)[N:17]=2)=O)=[C:8]([Cl:22])[C:7]([O:23][CH3:24])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(C1N=C(C2C=C(O)C3C(=CC(OC)=CC=3)N=2)SC=1)(C)C>>[Cl:22][C:8]1[C:7]([O:23][CH3:24])=[CH:6][CH:5]=[C:4]2[C:9]=1[N:10]=[C:11]([C:13]1[S:14][CH:15]=[C:16]([CH:18]3[CH2:21][CH2:20][CH2:19]3)[N:17]=1)[CH:2]=[C:1]2[OH:3]

Participants

3

Reactant 2

HCID 66730303N-(6-Acetyl-2-chloro-3-methoxyphenyl)-4-cyclobutylthiazole-2-carboxamideHCID 178487691HCID 178487691, compound

Product 1

HCID 178487690HCID 178487690, compoundYield 84%

Procedure

8-Chloro-7-methoxy-2-(4-cyclobutylthiazol-2-yl)quinolin-4-ol 269b was synthesized from compound 268b (5.68 g, 1 eq.) as a beige solid in 84% yield, following the procedure as described for compound 218a (80° C. overnight). 1H NMR (DMSO-d6, 400 MHz): δ (ppm) 1.87-1.95 (m, 1H), 1.96-2.07 (m, 1H), 2.23-2.35 (m, 4H), 3.67-3.76 (m, 1H), 4.02 (s, 3H), 7.51 (s, 1H), 7.53 (d, J=9.30 Hz, 1H), 7.63 (s, 1H), 8.11 (d, J=9.30 Hz, 1H), 11.89 (br s, 1H); MS (ESI, EI+): m/z=347 (MH+).

Sources & evidence

ORD record
ord-d44880ca45d84133abaef69ad8eacfda
Source dataset
uspto-grants-2013_02
Patent number
US08377962B2

Reaction notes

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