Ethanol → 2-(6-Amino-3-((1-benzyl-1H-pyrazole-4-carboxamido)methyl)-2-methylpyridin-4-yloxy)acetic acid

HRID 928400Notes

Reaction equation

HRID 928400 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][NH:10][C:11]([C:13]2[CH:14]=[N:15][N:16]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:17]=2)=[O:12])=[C:4]([O:25][CH2:26][C:27]([O:29]C)=[O:28])[CH:3]=1.CCO.O.[Li+].[OH-]>C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][NH:10][C:11]([C:13]2[CH:14]=[N:15][N:16]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:17]=2)=[O:12])=[C:4]([O:25][CH2:26][C:27]([OH:29])=[O:28])[CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 3939Lithium HydroxideHCID 58081178Methyl 2-(6-amino-3-((1-benzyl-1H-pyrazole-4-carboxamido)methyl)-2-methylpyridin-4-yloxy)acetate

Product 1

HCID 580813552-(6-Amino-3-((1-benzyl-1H-pyrazole-4-carboxamido)methyl)-2-methylpyridin-4-yloxy)acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(6-amino-3-((1-benzyl-1H-pyrazole-4-carboxamido)methyl)-2-methylpyridin-4-yloxy)acetate (28 mg, 0.051 mmol) was dissolved in THF, EtOH, H2O 2:1:1 (5 ml), then LiOH (4.31 mg, 0.103 mmol) was added and the reaction mixture was stirred at rt over night. After adjusting the pH to 4, the reaction mixture was evaporated, co-evaporated with Toluene (4 times) then dried under HV to get the title compound which was used for the next step without further purification. HPLC/MS (Method B) Rtb=0.43 min, MS [M+H]+=396.3.

Workup

  1. customthe reaction mixture was evaporated
  2. customthen dried under HV

Sources & evidence

ORD record
ord-05896458f23d4a81ab38d9e09b191052
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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