Sodium Hydroxide → Sodium 2-((4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazin-1-yl)methyl)isonicotinate

HRID 408881Notes

Reaction equation

HRID 408881 reaction equation
[CH:1]1([NH:5][C:6](=[O:34])[NH:7][C:8]2[CH:32]=[CH:31][C:11]([C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[CH:22]=[C:23]([CH:28]=[CH:29][N:30]=4)[C:24]([O:26]C)=[O:25])[CH2:16][CH2:15]3)=[O:13])=[CH:10][C:9]=2[F:33])[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+:36]>CO>[CH:1]1([NH:5][C:6](=[O:34])[NH:7][C:8]2[CH:32]=[CH:31][C:11]([C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[CH:22]=[C:23]([CH:28]=[CH:29][N:30]=4)[C:24]([O-:26])=[O:25])[CH2:16][CH2:15]3)=[O:13])=[CH:10][C:9]=2[F:33])[CH2:4][CH2:3][CH2:2]1.[Na+:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66661722Methyl 2-((4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazin-1-yl)methyl)isonicotinate

Product 1

HCID 66661564Sodium 2-((4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazin-1-yl)methyl)isonicotinateYield 95.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-((4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazin-1-yl)methyl)isonicotinate (1.746 mmol, 0.82 g) and sodium hydroxide (1.746 mmol, 0.070 g) were heated to reflux in methanol (20 mL) for 18 hours. The reaction mixture was concentrated at reduced pressure to afford the title compound (798 mg).

Workup

  1. concentrationThe reaction mixture was concentrated at reduced pressure

Sources & evidence

ORD record
ord-1b81ca74ec0142f385034f05e3366d19
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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