Diisopropylethylamine → HCID 178457856, compound
Reaction equation
F[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.Cl.[NH2:21][C@@H:22]1[CH2:27][CH2:26][C@H:25]([C:28]([NH:30][CH:31]([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1.CCN(C(C)C)C(C)C>C(#N)C.C(Cl)Cl>[CH:31]([NH:30][C:28]([C@H:25]1[CH2:24][CH2:23][C@@H:22]([NH:21][C:2]2[CH:3]=[C:4]([O:5][CH2:6][CH2:7][N:8]3[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[CH:14]=[CH:15][C:16]=2[N+:17]([O-:19])=[O:18])[CH2:27][CH2:26]1)=[O:29])([CH3:33])[CH3:32]Participants
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 1-(2-(3-fluoro-4-nitrophenoxy)ethyl)piperidine (220 mg, 0.820 mmol) and cis-4-amino-N-isopropylcyclohexanecarboxamide hydrochloride (190 mg, 0.861 mmol) in ACN (0.8 mL) was added DIPEA (0.301 mL, 1.722 mmol). The mixture was heated at 80° C. in a sealed tube for 14 hours, and then additional cis-4-amino-N-isopropylcyclohexanecarboxamide hydrochloride (38 mg, 0.172 mmol) and DIPEA (0.100 mL, 0.574 mmol) were added. The resulting mixture was heated an additional 24 hours. The mixture was diluted with DCM (5 mL), washed with water/brine mixture, brine, and the organic layer was dried over Na2SO4, filtered and evaporated to afford cis-N-isopropyl-4-(2-nitro-5-(2-(piperidin-1-yl)ethoxy)phenylamino)cyclohexanecarboxamide.
Workup
- temperatureThe resulting mixture was heated an additional 24 hours
- washwashed with water/brine mixture, brine
- dry with materialthe organic layer was dried over Na2SO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-f7db9cb14e984deb8ecc85888c7df7bb
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115127B2
Reaction notes
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