Sodium Methoxide → 1-[4-(Methoxy)-6-(4-methyl-1-piperazinyl)-1,3,5-triazin-2-yl]-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide

HRID 1678424Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[N:5]=[C:4]([N:15]2[CH2:20][CH2:19][CH:18]([C:21]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:33])[F:32])=[O:22])[CH2:17][CH2:16]2)[N:3]=1.[CH3:35][O-:36].[Na+]>>[CH3:35][O:36][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[N:5]=[C:4]([N:15]2[CH2:20][CH2:19][CH:18]([C:21]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:33])[F:32])=[O:22])[CH2:17][CH2:16]2)[N:3]=1

Participants

Reactant 2

HCID 10942334Sodium Methoxide

HCID 866443141-[4-chloro-6-(4-methyl-1-piperazinyl)-1,3,5-triazin-2-yl]-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide

Product 1

HCID 252619291-[4-(Methoxy)-6-(4-methyl-1-piperazinyl)-1,3,5-triazin-2-yl]-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamideYield 4.6%

Conditions

Temperature: 80 °C

Procedure

⅕ of the suspension prepared in step b of Example 20 (0.542 mmol, 1.00 equiv) was concentrated under reduced pressure. Then, sodium methoxide (1.24 mL of 25 wt % solution in MeOH, 5.42 mmol, 10.0 equiv) was added. The resulting mixture was heated to 80° C. for 1 h. The final solution was purified by reverse-phase HPLC (Sunfire, 20-40% CH3CN, H2O, 0.1% TFA, 12 min) to afford 12.2 mg of the title compound. MS (ES+): m/e 493.8 [M+H]+.

Workup

customThe final solution was purified by reverse-phase HPLC (Sunfire, 20-40% CH3CN, H2O, 0.1% TFA, 12 min)

Sources & evidence

ORD record: ord-45b65ea4d661452abf67531437ed7660
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008483B2

Reaction notes

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