Lithium Hydroxide → (+/-)-4-(1-{[6-(4-cyclopropyl-1H-pyrazol-1-yl)pyridin-3-yl]amino}butyl)benzoic acid

HRID 1892802Notes

Reaction equation

HRID 1892802 reaction equation
[CH:1]1([C:4]2[CH:5]=[N:6][N:7]([C:9]3[N:14]=[CH:13][C:12]([NH:15][CH:16]([C:20]4[CH:30]=[CH:29][C:23]([C:24]([O:26]CC)=[O:25])=[CH:22][CH:21]=4)[CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=3)[CH:8]=2)[CH2:3][CH2:2]1.O1CCCC1.[OH-].[Li+]>CO>[CH:1]1([C:4]2[CH:5]=[N:6][N:7]([C:9]3[N:14]=[CH:13][C:12]([NH:15][CH:16]([C:20]4[CH:30]=[CH:29][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=4)[CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=3)[CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86669097Ethyl 4-(1-((6-(4-cyclopropyl-1H-pyrazol-1-yl)pyridin-3-yl)amino)butyl)benzoate

Product 1

HCID 68157702(+/-)-4-(1-{[6-(4-cyclopropyl-1H-pyrazol-1-yl)pyridin-3-yl]amino}butyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (+/−)-ethyl 4-(1-{[6-(4-cyclopropyl-1H-pyrazol-1-yl)pyridin-3-yl]amino}butyl)benzoate (26 mg, 0.064 mmol) was dissolved in methanol (0.13 ml) and tetrahydrofuran (0.070 ml) and treated with aqueous 2.0M lithium hydroxide (64 ul, 0.13 mmol). The mixture was stirred at ambient temperature for 12 hours. The reaction was concentrated in vacuo and the residue was acidified with aqueous 1.0M hydrochloric acid. The crude product was concentrated in vacuo a second time and was used without further purification.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. concentrationThe crude product was concentrated in vacuo a second time
  3. customwas used without further purification

Sources & evidence

ORD record
ord-c80f43e13d104edd88b48cbbad0ac9ff
Source dataset
uspto-grants-2013_08
Patent number
US08507533B2

Reaction notes

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