Methanol → HCID 68245578, compound

HRID 1403673Notes

Reaction equation

HRID 1403673 reaction equation
C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([C:14]1[CH:19]=[C:18]([C:20](=[O:28])[NH:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[CH:17]=[CH:16][C:15]=1[CH:29]([NH2:31])[CH3:30])[CH:10]=[CH:9][CH:8]=2)=[O:4].[Li+].[OH-:33].[CH3:34][OH:35]>C1COCC1>[C:11]([O:33][C:34]([NH:31][CH:29]([C:15]1[CH:16]=[CH:17][C:18]([C:20](=[O:28])[NH:21][C:22]2[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=2)=[CH:19][C:14]=1[C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[CH:13]=[C:5]([C:3]([OH:2])=[O:4])[NH:6]2)[CH3:30])=[O:35])([CH3:14])([CH3:12])[CH3:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 67411495HCID 67411495, compound

Product 1

HCID 68245578HCID 68245578, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-[2-(1-amino-ethyl)-5-(pyridin-4-ylcarbamoyl)-phenyl]-1H-indole-2-carboxylic acid methyl ester (600 μmol) in THF (2.4 ml) and MeOH (2.4 ml) was added a 1N LiOH solution (2.4 ml). The reaction mixture was stirred at 40° C. for 6 hours. The reaction mixture was diluted with 1N LION and extracted with EtOAc. The aqueous layer is acidified with a 20% citric acid solution and extracted again with EtOAc. The combined organic layers were dried over MgSO4 and the solvent was removed under reduced pressure.

Workup

  1. additionThe reaction mixture was diluted with 1N LION
  2. extractionextracted with EtOAc
  3. extractionextracted again with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ad491719c22c4490ac140b040933a5c6
Source dataset
uspto-grants-2014_12
Patent number
US08912209B2

Reaction notes

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