Sodium Methoxide → HCID 58397852, compound

HRID 451510Notes

Reaction equation

HRID 451510 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]3[N:31]=[C:18]4[C:19]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=5)=[CH:20][CH:21]=[CH:22][N:17]4[N:16]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[CH3:32][O-:33].[Na+]>CO>[F:30][C:25]1[CH:24]=[C:23]([C:19]2[C:18]3[N:17]([N:16]=[C:15]([NH:14][CH:11]4[CH2:12][CH2:13][N:8]([C:6]5[CH:5]=[CH:4][N:3]=[C:2]([O:33][CH3:32])[N:7]=5)[CH2:9][CH2:10]4)[N:31]=3)[CH:22]=[CH:21][CH:20]=2)[CH:28]=[CH:27][C:26]=1[F:29]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 58397891HCID 58397891, compound

Product 1

HCID 58397852HCID 58397852, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of N-(1-(2-chloropyrimidin-4-yl)piperidin-4-yl)-8-(3,4-difluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (example 195) (88 mg, 0.155 mmol) in MeOH (2.0 mL) was added sodium methoxide solution (30% in MeOH, 41 μL, 0.22 mmol) and the reaction mixture was heated in the microwave at 120° C. for 2 h. The mixture was then evaporated. Purification by chromatography (silica gel, 20 g, 0 to 100% methanol in dichloromethane) afforded the title compound (71 mg, 81%) as a white foam.

Workup

  1. customThe mixture was then evaporated
  2. customPurification by chromatography (silica gel, 20 g, 0 to 100% methanol in dichloromethane)

Sources & evidence

ORD record
ord-7a64f8d5e9d446b4876681ed4fb04cb4
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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