HCID 178462204, compound → HCID 178461855, compound
Reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10](=O)[NH:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[NH:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([C:26]#[N:27])[CH2:22][CH2:21]1)[CH3:9])(C)(C)C>CC(O)=O>[NH2:7][C@H:8]([C:10]1[N:19]([C@H:20]2[CH2:25][CH2:24][C@H:23]([C:26]#[N:27])[CH2:22][CH2:21]2)[C:13]2[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=2[N:11]=1)[CH3:9]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of {(S)-1-[2-(trans-4-cyanocyclohexylamino)-4-fluorophenylcarbamoyl]ethyl}carbamic acid tert-butyl ester (195 mg, 0.48 mmol) in AcOH (2 mL) was heated at 80° C. under a nitrogen atmosphere for 1 h, then at 90° C. for 2 h and finally at 110° C. for 16 h. The volatiles were removed under reduced pressure and the resulting residue dissolved in 6N HCl (5 mL) and heated at reflux temperature for 2 h. The volatiles were removed in vacuo and the resulting residue dissolved in an aqueous solution of NaHCO3 and extracted with EtOAc (×3). The combined organic fractions were washed with water, dried and concentrated in vacuo to afford the title compound as a brown solid (100 mg, 72%). LCMS (Method C): RT 2.01 min [M+H]+ 287.1.
Workup
- waitfinally at 110° C. for 16 h
- customThe volatiles were removed under reduced pressure
- dissolutionthe resulting residue dissolved in 6N HCl (5 mL)
- temperatureheated
- temperatureat reflux temperature for 2 h
- customThe volatiles were removed in vacuo
- dissolutionthe resulting residue dissolved in an aqueous solution of NaHCO3
- extractionextracted with EtOAc (×3)
- washThe combined organic fractions were washed with water
- customdried
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-8aa1a6129ad54fd283e49a058c21d5a0
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653089B2
Reaction notes
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