Sodium Methoxide → 5-(4-Chlorophenyl)-4-cyclopropyl-2-[(5-{2-[3-(trifluoromethyl)phenyl]propan-2-yl}-4H-1,2,4-triazol-3-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714683Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:20][NH2:21])=O)[N:9]=2)=[CH:4][CH:3]=1.Cl.[CH3:23][C:24]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=1)([CH3:28])[C:25](=N)[NH2:26].C[O-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]3[NH:26][C:25]([C:24]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:36])([F:38])[F:37])[CH:30]=4)([CH3:28])[CH3:23])=[N:21][N:20]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 180 °C

Procedure

42 mg (0.14 mmol) of the compound from Example 21A were dissolved in 1.2 ml of DMF, 40 mg (0.15 mmol) of 2-methyl 2-[3-(trifluoromethyl)phenyl]propaneimidamide hydrochloride and 9 mg (0.16 mmol) of sodium methoxide were added and the mixture was stirred in a microwave reactor at 180° C. for 2 h. After cooling to RT, the mixture was purified directly by preparative HPLC [Method 19]. This gave 2 mg (3% of theory) of the target compound as a colorless foam.

Workup

temperatureAfter cooling to RT
customthe mixture was purified directly by preparative HPLC [Method 19]

Sources & evidence

ORD record: ord-b1b7312341af48dc84fa7e3f795de816
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187466B2

Reaction notes

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