Sodium Hydroxide → Sodium 6-((4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazin-1-yl)methyl)picolinate

HRID 408877Notes

Reaction equation

HRID 408877 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[N:26]=[C:25]([C:27]([O:29]C)=[O:28])[CH:24]=[CH:23][CH:22]=4)[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[N:26]=[C:25]([C:27]([O-:29])=[O:28])[CH:24]=[CH:23][CH:22]=4)[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 58055793HCID 58055793, compound

Product 1

HCID 66661327Sodium 6-((4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazin-1-yl)methyl)picolinateYield 79.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 6-((4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazin-1-yl)methyl)picolinate (400 mg, 0.852 mmol) and sodium hydroxide (35 mg, 0.852 mmol) were combined and heated to reflux for 18 hours in methanol. The reaction mixture was concentrated at reduced pressure to afford the title compound (323 mg).

Workup

  1. temperatureheated
  2. concentrationThe reaction mixture was concentrated at reduced pressure

Sources & evidence

ORD record
ord-7b60709f6fe248068aaa42dc7c002603
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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