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

HRID 515281Notes

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:47]=[CH:46][C:21]([CH2:22][CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([C:36]([OH:45])([C:41]([F:44])([F:43])[F:42])[C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=3)[CH2:25][CH2:24]2)=[CH:20][CH:19]=1>O1CCOCC1>[F:40][C:37]([F:38])([F:39])[C:36]([C:33]1[CH:32]=[CH:31][C:30]([CH2:29][N:26]2[CH2:25][CH2:24][CH:23]([CH2:22][C:21]3[CH:20]=[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:47][CH:46]=3)[CH2:28][CH2:27]2)=[CH:35][CH:34]=1)([OH:45])[C:41]([F:44])([F:43])[F:42]

Participants

Conditions

Temperature: 130 °C

Procedure

Phenyl pyridin-4-ylcarbamate (1.680 mmol, 0.36 g) was added to a stirred solution of 2-(4-((4-(4-aminobenzyl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (1.120 mmol, 0.5 g) in dioxane (20 mL) and the mixture heated in a microwave for 10 minutes at 130° C. followed by 5 minutes at 130° C. The mixture was washed with water (10 mL) and the organic phase dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by HPLC and concentrated under reduced pressure to afford the title compound (168 mg). MS (ESI) m/z 567.5 [M+H]+

Workup

washThe mixture was washed with water (10 mL)
dry with materialthe organic phase dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by HPLC
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-dd75a4cf19ab4696ae56c897acbe1636
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108939B2

Reaction notes

Loading…