Diisopropylethylamine → HCID 86670956, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([OH:31])([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[C:32](Cl)(=O)[O:33]C1C=CC([N+]([O-])=O)=CC=1.Cl.[O:46]1[CH2:50][CH2:49][C@H:48]([NH2:51])[CH2:47]1.C(N(C(C)C)C(C)C)C>ClCCl>[F:26][C:23]([F:24])([F:25])[C:22]([C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:12]2[CH2:11][CH2:10][CH:9]([S:8][C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:32]([NH:51][C@H:48]4[CH2:49][CH2:50][O:46][CH2:47]4)=[O:33])=[CH:3][CH:4]=3)[CH2:14][CH2:13]2)=[CH:17][CH:18]=1)([OH:31])[C:27]([F:30])([F:29])[F:28]Participants
Procedure
2-(4-((4-(4-Aminophenylthio)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (1.076 mmol, 500 mg), and 4-nitrophenyl carbonochloridate (1.076 mmol, 217 mg) were combined in dichloromethane (10 mL) and the reaction mixture stirred at room temperature for 1 hour. (S)-Tetrahydrofuran-3-amine hydrochloride (2.153 mmol, 266 mg), and N-ethyl-N-isopropylpropan-2-amine (2.153 mmol, 0.356 mL, 278 mg) were added and the reaction mixture stirred for 30 minutes. The reaction mixture was washed with water, and the organic layer separated, dried, and concentrated under vacuum. The residue was purified by silica column chromatography (eluting with 0-10% methanol/dichloromethane gradient) to afford the title compound (284 mg). MS m/z 578.2 [M+H]+
Workup
- stirringthe reaction mixture stirred for 30 minutes
- washThe reaction mixture was washed with water
- customthe organic layer separated
- customdried
- concentrationconcentrated under vacuum
- customThe residue was purified by silica column chromatography (eluting with 0-10% methanol/dichloromethane gradient)
Sources & evidence
- ORD record
- ord-f691b1be7f4341a7987a6b0de5ba5f8c
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108939B2
Reaction notes
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