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

HRID 1807795Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:16])OC2C=CC=CC=2)=[CH:3][CH:2]=1.[NH2:17][C:18]1[CH:19]=[C:20]([C:24]([N:26]2[CH2:31][CH2:30][N:29]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([C:39]([OH:48])([C:44]([F:47])([F:46])[F:45])[C:40]([F:43])([F:42])[F:41])=[CH:35][CH:34]=3)[CH2:28][CH2:27]2)=[O:25])[CH:21]=[CH:22][CH:23]=1>O1CCOCC1>[F:47][C:44]([F:45])([F:46])[C:39]([C:36]1[CH:35]=[CH:34][C:33]([CH2:32][N:29]2[CH2:28][CH2:27][N:26]([C:24]([C:20]3[CH:19]=[C:18]([NH:17][C:8]([NH:7][C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)=[O:16])[CH:23]=[CH:22][CH:21]=3)=[O:25])[CH2:31][CH2:30]2)=[CH:38][CH:37]=1)([OH:48])[C:40]([F:43])([F:42])[F:41]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of phenyl pyridin-4-ylcarbamate (1.430 mmol, 306 mg) and (3-aminophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone (0.954 mmol, 440 mg) in dioxane was heated in a Reactivial at 100° C. (heating block temperature) for 2 days. Chromatography on silica (eluting with a gradient of dichloromethane to dichloromethane/methanol) gave the title compound (200 mg).

Workup

temperature(heating block temperature) for 2 days
washChromatography on silica (eluting with a gradient of dichloromethane to dichloromethane/methanol)

Sources & evidence

ORD record: ord-05ef45a5a7d94bce925b01c1043fd5d0
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357679B2

Reaction notes

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