3-(Trifluoromethyl)phenyl isocyanate → HCID 59149897, compound

HRID 655555Notes

Reaction equation

HRID 655555 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH3:14][C@@H:15]1[NH:20][CH2:19][CH2:18][N:17]([CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[C:16]1=[O:30]>C(#N)C>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:20]2[CH2:19][CH2:18][N:17]([CH2:21][CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)[C:16](=[O:30])[C@@H:15]2[CH3:14])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 67079895HCID 67079895, compound2×

Product 1

HCID 59149897HCID 59149897, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

3-(Trifluoromethyl)phenyl isocyanate (30 mg, 0.15 mmol) was added to a solution of (S)-3-methyl-1-(3-piperidin-1-yl-propyl)-piperazin-2-one (intermediate 20; 30 mg, 0.13 mmol) in acetonitrile (1 ml). The solution was heated at 60° C. for 15 min under microwave irradiation, then evaporated. Chromatography (SiO2; dichloromethane/methanol/25% aq. ammonia solution 90:10:0.25) produced the title compound (46 mg, 86%). Colorless gum, MS (ISP)=427.3 (M+H)+.

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-b52b495100b54c828453ef96c2d14949
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

Loading…