Dimethylformamide → 5-Methylthio-6-trifluoromethyl-1-{3-[2-(3-pyridyl)thiazol-4-yl]phenylcarbamoyl} indoline

HRID 989218Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[S:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[C:19](C1NC=CN=1)(C1NC=CN=1)=[O:20].[CH3:31][S:32][C:33]1[CH:34]=[C:35]2[C:39](=[CH:40][C:41]=1[C:42]([F:45])([F:44])[F:43])[NH:38][CH2:37][CH2:36]2.CN(C)C=O>C(Cl)(Cl)Cl.ClCCl.O>[CH3:31][S:32][C:33]1[CH:34]=[C:35]2[C:39](=[CH:40][C:41]=1[C:42]([F:45])([F:43])[F:44])[N:38]([C:19](=[O:20])[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[N:9]=[C:10]([C:13]4[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=4)[S:11][CH:12]=3)[CH:3]=1)[CH2:37][CH2:36]2

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 4-(3-aminophenyl)-2-(3-pyridyl)-thiazole (0.76 g, 3 mmol) in chloroform (30 ml) was added to a solution of carbonyl diimidazole (0.49 g, 3 mmol) in dichloromethane (10 ml). After 1 h the mixture was evaporated 5-Methylthio-6-trifluoromethyl indoline (0.7 g, 3 mmol) and N,N-dimethylformamide (20 ml) were added. The mixture was heated at 100° C. for 1 h, then diluted with water (50 ml). Filtraton and evaporated afforded a yellow solid (1.1 g). Recrystallisation from ethyl acetate-petrol afforded the title compound as a white solid (0.53 g, 35%), m.p. 154-5° C.

Workup

additionwere added
customFiltraton and evaporated

Sources & evidence

ORD record: ord-af60f4c3e9044980a3c1242e95c8d9b3
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06638953B2

Reaction notes

Loading…