3-Chloro-4-methylphenyl isocyanate → HCID 118288518, compound

HRID 530630Notes

Reaction equation

HRID 530630 reaction equation
[F:1][C:2]([F:23])([F:22])[C@@H:3]([OH:21])[CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH2:6]1.[Cl:24][C:25]1[CH:30]=[C:29]([N:31]=[C:32]=[O:33])[CH:28]=[CH:27][C:26]=1[CH3:34]>C(#N)C>[F:23][C:2]([F:1])([F:22])[C@@H:3]([O:21][C:32](=[O:33])[NH:31][C:29]1[CH:28]=[CH:27][C:26]([CH3:34])=[C:25]([Cl:24])[CH:30]=1)[CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH:7]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:15][CH:16]=2)[CH2:6]1

Participants

4

Reactant 2

HCID 628323-Chloro-4-methylphenyl isocyanateHCID 117870769HCID 117870769, compound

Product 1

HCID 118288518HCID 118288518, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-1,1,1-Trifluoro-3-[2-(4-trifluoromethyl-phenyl)-morpholin-4-yl]-propan-2-ol (50 mg, 146 μmol) and 2-chloro-4-isocyanato-1-methylbenzene (prepared by a similar procedure as for intermediate A, 24.4 mg, 146 μmol) were combined in acetonitrile (1 mL). A mixture was stirred at room temperature overnight and evaporated. The residue was purified by flash chromatography (20% EtOAc/hexanes) to provide (3-chloro-4-methylphenyl)-carbamic acid (S)-2,2,2-trifluoro-1-[2-(4-trifluoromethyl-phenyl)-morpholin-4-ylmethyl]-ethyl ester, which was converted to the HCl salt to afford (3-chloro-4-methylphenyl)-carbamic acid (S)-2,2,2-trifluoro-1-[2-(4-trifluoromethyl-phenyl)-morpholin-4-ylmethyl]-ethyl ester hydrochloride as a white solid (15 mg). (M+H)+=511 m/e.

Workup

  1. customevaporated
  2. customThe residue was purified by flash chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cb6c7ccd8bbc4474bef54f0b465c8de9
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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