CHLOROMETHYL ISOBUTYRATE → HCID 178424803, compound

HRID 403187Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]([NH:12][CH:13]1[CH2:15][CH:14]1[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:26]=[CH:25][N:24]([C:27]3[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=3)[N:23]=2)=[CH:18][CH:17]=1)=[S:11].[C:38]([O:43][CH2:44]Cl)(=[O:42])[CH:39]([CH3:41])[CH3:40]>C(Cl)(Cl)Cl>[C:38]([O:43][CH2:44][S:11]/[C:10](=[N:9]\[C:3]1[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])/[NH:12][CH:13]1[CH2:15][CH:14]1[C:16]1[CH:17]=[CH:18][C:19]([C:22]2[N:26]=[CH:25][N:24]([C:27]3[CH:28]=[CH:29][C:30]([O:33][C:34]([F:36])([F:37])[F:35])=[CH:31][CH:32]=3)[N:23]=2)=[CH:20][CH:21]=1)(=[O:42])[CH:39]([CH3:41])[CH3:40]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1-(2,6-dimethylphenyl)-3-(2-(4-(1-(4-(trifluoromethoxy)-phenyl)-1H-1,2,4-triazol-3-yl)phenyl)cyclopropyl)thiourea (75 mg, 0.143 mmol) in chloroform (CHCl3; 0.72 mL) was added chloromethyl isobutyrate (31.1 mg, 0.172 mmol). The mixture was heated at 100° C. for 1 h. The mixture was cooled to 25° C., and the residue was purified by silica gel chromatography (EtOAc-hexanes gradient) to afford the title compound (17.3 mg, 19%) as a yellow oil: IR νmax 3332 (br), 3124, 2976, 2939, 1739, 1631, 1590, 1518, 1264, 1171, 986 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.54 (s, 1H), 8.09 (d, J=8.3 Hz, 2H), 7.79 (d, J=9.0 Hz, 2H), 7.37 (d, J=8.3 Hz, 2H), 7.20 (d, J=7.2 Hz, 2H), 7.02 (d, J=7.5 Hz, 2H), 6.88 (t, J=7.5 Hz, 1H), 5.65 (br s, 2H), 2.88 (br s, 1H), 2.68-2.52 (m, 1H), 2.10 (s, 6H), 1.82-1.46 (m, 2H), 1.46-1.22 (m, 2H), 1.22-1.18 (m, 6H); ESIMS m/z 624 (M+H).

Workup

temperatureThe mixture was cooled to 25° C.
customthe residue was purified by silica gel chromatography (EtOAc-hexanes gradient)

Sources & evidence

ORD record: ord-5374e22024584e1baad916cc50a1f59f
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748340B2

Reaction notes

Loading…