4-(Trifluoromethyl)phenyl isocyanate → HCID 25252815, compound

HRID 2063497Notes

Reaction equation

HRID 2063497 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2[C:8]([CH3:17])=[N:9][O:10][C:11]=2[C@H:12]2[CH2:16][CH2:15][CH2:14][NH:13]2)=[CH:4][CH:3]=1.[N:20]([C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1)=[C:21]=[O:22]>ClCCl>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2[C:8]([CH3:17])=[N:9][O:10][C:11]=2[C@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:21]([NH:20][C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=2)=[O:22])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 57650311HCID 57650311, compound

Product 1

HCID 25252815HCID 25252815, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-4-(4-chlorobenzyl)-3-methyl-5-(pyrrolidin-2-yl)isoxazole (20 mg, 0.07 mmol) in dichloromethane (2 mL) was added 1-isocyanato-4-(trifluoromethyl)benzene (13 mg, 0.07 mmol). The reaction mixture was stirred at room temperature for 10 min and concentrated in vacuo. Purification of the resulting residue by semi-preparative HPLC afforded (R)-2-(4-(4-chlorobenzyl)-3-methylisoxazol-5-yl)-N-(4-(trifluoromethyl)phenyl)pyrrolidine-1-carboxamide (20 mg, 62%).

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification of the resulting residue by semi-preparative HPLC

Sources & evidence

ORD record
ord-610597396aeb4c6cb99617a20917a083
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

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