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-methoxyphenyl)-3-(pyridin-4-yl)urea

HRID 1807767Notes

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][CH3:34].[N:35]1[CH:40]=[CH:39][C:38]([NH:41][C:42](=O)[O:43]C2C=CC=CC=2)=[CH:37][CH:36]=1>O1CCOCC1>[F:30][C:28]([F:31])([F:29])[C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:13]2[CH2:12][CH2:11][N:10]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:42]([NH:41][C:38]4[CH:39]=[CH:40][N:35]=[CH:36][CH:37]=4)=[O:43])=[C:3]([O:33][CH3:34])[CH:4]=3)=[O:9])[CH2:15][CH2:14]2)=[CH:18][CH:19]=1)([OH:32])[C:24]([F:25])([F:26])[F:27]

Participants

Conditions

Temperature: 80 °C

Procedure

(4-Amino-3-methoxyphenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone (0.407 mmol, 200 mg) and phenyl pyridin-4-ylcarbamate (0.610 mmol, 131 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 (12.2 mg). MS (ESI) m/z 612.3 [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-179d55a01c4f4edc84f14987f1e8b5b9
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357679B2

Reaction notes

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