Carbamic acid, 4-pyridinyl-, phenyl ester → 1-(4-(4-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)-2-(trifluoromethoxy)phenyl)-3-(pyridin-4-yl)urea

HRID 1807771Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[O:33][C:34]([F:37])([F:36])[F:35].[N:38]1[CH:43]=[CH:42][C:41]([NH:44][C:45](=O)[O:46]C2C=CC=CC=2)=[CH:40][CH:39]=1>O1CCOCC1>[F:27][C:24]([F:25])([F:26])[C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:13]2[CH2:14][CH2:15][N:10]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:45]([NH:44][C:41]4[CH:42]=[CH:43][N:38]=[CH:39][CH:40]=4)=[O:46])=[C:3]([O:33][C:34]([F:36])([F:37])[F:35])[CH:4]=3)=[O:9])[CH2:11][CH2:12]2)=[CH:18][CH:19]=1)([OH:32])[C:28]([F:29])([F:30])[F:31]

Participants

Conditions

Temperature: 80 °C

Procedure

(4-Amino-3-(trifluoromethoxy)phenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone (0.367 mmol, 200 mg) and phenyl pyridin-4-ylcarbamate (0.550 mmol, 118 mg) were combined in dioxane (2 mL) and heated to 80° C. overnight in a reactivial. The reaction mixture was concentrated under vacuum and the residue was purified by column chromatography (dichloromethane—4% methanol/dichloromethane) to afford title compound (11.7 mg). MS (ESI) m/z 666.3 [M+H]+

Workup

concentrationThe reaction mixture was concentrated under vacuum
customthe residue was purified by column chromatography (dichloromethane—4% methanol/dichloromethane)

Sources & evidence

ORD record: ord-fb0e0b00b51442b0b8bdafdbd3245251
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357679B2

Reaction notes

Loading…