Triethylamine → HCID 86670977, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH: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)[CH3:9])=[CH:4][CH:3]=1.Cl[C:34](OC1C=CC([N+]([O-])=O)=CC=1)=[O:35].[NH2:46][CH2:47][C:48]([CH3:51])([OH:50])[CH3:49].C(N(CC)CC)C>O1CCCC1>[F:27][C:24]([F:25])([F:26])[C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:13]2[CH2:12][CH2:11][CH:10]([CH:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:34]([NH:46][CH2:47][C:48]([OH:50])([CH3:51])[CH3:49])=[O:35])=[CH:3][CH:4]=3)[CH3:9])[CH2:15][CH2:14]2)=[CH:18][CH:19]=1)([OH:32])[C:28]([F:31])([F:29])[F:30]Participants
6
Procedure
2-(4-((4-(1-(4-Aminophenyl)ethyl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (0.178 mmol, 82 mg) and 4-nitrophenyl chloroformate (0.178 mmol, 35.9 mg) were combined in tetrahydrofuran (2 mL) and the reaction stirred at room temperature for 1 hour. 1-Amino-2-methylpropan-2-ol (0.178 mmol, 15.87 mg) and triethylamine (0.534 mmol, 54.1 mg) were added and the mixture stirred at room temperature overnight. The mixture was concentrated under reduced pressure and the resulting residue purified by silica gel column chromatography (eluting with dichloromethane to 10% methanol/dichloromethane) to afford the title compound (16 mg). MS (ESI) m/z 576.2 [M+H]+
Workup
- stirringthe mixture stirred at room temperature overnight
- concentrationThe mixture was concentrated under reduced pressure
- customthe resulting residue purified by silica gel column chromatography (eluting with dichloromethane to 10% methanol/dichloromethane)
Sources & evidence
- ORD record
- ord-0a140b5a92a2460b8e331f16d6df4fea
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108939B2
Reaction notes
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