Ethanamine, 2,2,2-trifluoro- → HCID 14625223, compound
Reaction equation
Cl[C:2](OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].[NH2:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([Cl:21])[CH:16]=1.[F:22][C:23]([F:27])([F:26])[CH2:24][NH2:25].CCN(C(C)C)C(C)C>C1COCC1>[Cl:21][C:17]1[CH:16]=[C:15]([NH:14][C:2]([NH:25][CH2:24][C:23]([F:27])([F:26])[F:22])=[O:3])[CH:20]=[CH:19][N:18]=1Participants
6
Conditions
- Temperature
- 60 °C
Procedure
To 4-nitrophenyl chloroformate (2.91 g, 14.5 mmol) in THF (35 mL) was added 4-amino-2-chloropyridine (2.08 g, 16.2 mmol) and the reaction stirred at 60° C. for 2 hours. After cooling to room temperature 2,2,2-trifluoroethylamine (1.26 mL, 15.9 mmol) and DIPEA (7.5 mL, 43.4 mmol) were added and the reaction stirred at room temperature for 18 hours. The reaction was concentrated in vacuo and the residue partitioned between 1M NaOH (40 mL) and EtOAc (2×50 mL). The combined organic phases were washed with brine (60 mL), dried over MgSO4, filtered and concentrated in vacuo. The resulting yellow solid was suspended in CH2Cl2, filtered and washed with CH2Cl2 to give the product as a pale yellow solid (1.72 g).
Workup
- additionwere added
- stirringthe reaction stirred at room temperature for 18 hours
- concentrationThe reaction was concentrated in vacuo
- customthe residue partitioned between 1M NaOH (40 mL) and EtOAc (2×50 mL)
- washThe combined organic phases were washed with brine (60 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- filtrationfiltered
- washwashed with CH2Cl2
Sources & evidence
- ORD record
- ord-7f63bb8deacc4404883ca666f54cf83d
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895745B2
Reaction notes
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