Triethylamine → HCID 57489531, compound

HRID 1961553Notes

Reaction equation

HRID 1961553 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[CH:10]=[CH:9][C:8]([C:11]3[CH2:15][C:14]([C:20]4[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[C:23]([Cl:30])=[C:22]([Cl:31])[CH:21]=4)([C:16]([F:19])([F:18])[F:17])[O:13][N:12]=3)=[CH:7][CH:6]=2)[CH2:2]1.C(N(CC)CC)C.[N:39]([CH3:42])=[C:40]=[O:41]>CN(C=O)C>[Cl:31][C:22]1[CH:21]=[C:20]([C:14]2([C:16]([F:17])([F:18])[F:19])[O:13][N:12]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([CH:3]4[CH2:4][N:1]([C:40]([NH:39][CH3:42])=[O:41])[CH2:2]4)=[CH:6][CH:7]=3)[CH2:15]2)[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[C:23]=1[Cl:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 86661741HCID 86661741, compound

Product 1

HCID 57489531HCID 57489531, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(4-(azetidin-3-yl)phenyl)-5-(3,4-dichloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (0.05 mmol) was dissolved in DMF (1 mL); triethylamine (0.20 mmol) was added, followed by a solution isocyanatomethane. The resulting solution was stirred at ambient temperature for 16 hours. The solvent was removed under reduced pressure and the crude product purified by preparative HPLC to give 3-(4-(5-(3,4-dichloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-N-methylazetidine-1-carboxamide (11.2 mg) MH+ 540.1; retention time 6.14 minutes.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product purified by preparative HPLC

Sources & evidence

ORD record
ord-e66f3176d3f740969720eb27f5966ed9
Source dataset
uspto-grants-2013_04
Patent number
US08415310B2

Reaction notes

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