Carbamic acid, 4-pyridinyl-, phenyl ester → HCID 52919309, compound
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][C:19]=1[F:48]>O1CCOCC1>[F:48][C:19]1[CH:20]=[C:21]([CH2:22][CH:23]2[CH2:24][CH2:25][N:26]([CH2:29][C:30]3[CH:31]=[CH:32][C:33]([C:36]([OH:45])([C:41]([F:42])([F:43])[F:44])[C:37]([F:39])([F:40])[F:38])=[CH:34][CH:35]=3)[CH2:27][CH2:28]2)[CH:46]=[CH:47][C:18]=1[NH:17][C:8]([NH:7][C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1)=[O:16]Participants
4
Conditions
- Temperature
- 130 °C
Procedure
Phenyl pyridin-4-ylcarbamate (1.933 mmol, 0.414 g) was added to a stirred solution of 2-(4-((4-(4-amino-3-fluorobenzyl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (1.292 mmol, 0.6 g) in dioxane (6 mL) and the mixture heated in a microwave for 10 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 silica gel column chromatography (eluting with 1% to 10% methanol/dichloromethane) to afford the title compound (271 mg). MS (ESI) m/z 585.3 [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 silica gel column chromatography (eluting with 1% to 10% methanol/dichloromethane)
Sources & evidence
- ORD record
- ord-6d30114a342944179bbdf5a9cca13777
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108939B2
Reaction notes
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