Hydrochloric Acid → HCID 45377841, compound

HRID 1627228Notes

Reaction equation

HRID 1627228 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21](=[O:30])[NH:22][CH2:23][C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[CH:16]=1)=[CH:10][CH:9]=2)=[O:5])C.[OH-].[Na+].Cl>C(O)C.O>[N:27]1[CH:28]=[CH:29][C:24]([CH2:23][NH:22][C:21]([C:17]2[CH:16]=[C:15]([C:11]3[CH:12]=[C:13]4[C:8](=[CH:9][CH:10]=3)[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:14]4)[CH:20]=[CH:19][N:18]=2)=[O:30])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 45377425HCID 45377425, compound

Product 1

HCID 45377841HCID 45377841, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To 5-{2-[(Pyridin-4-ylmethyl)-carbamoyl]-pyridin-4-yl}-1H-indole-2-carboxylic acid ethyl ester (160 mg, 0.4 mmol) in ethanol (4 ml) is added aqueous sodium hydroxide (2N) and the mixture is stirred at 70° C. for 2 hours. The reaction is cooled, diluted with water (30 ml), acidified with aqueous HCl (3N) to pH 4-5, extracted with dichloromethane (50 ml). The combined organic layer is dried (sodium sulfate), filtered and evaporated in vacuo to give the title compound, 95 mg, 64%, LC/MS ESI m/z (M+H)+=273.8.

Workup

  1. temperatureThe reaction is cooled
  2. extractionextracted with dichloromethane (50 ml)
  3. dry with materialThe combined organic layer is dried (sodium sulfate)
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-1d10eb4663c14fd98cf3faa371ce6f2a
Source dataset
uspto-grants-2014_07
Patent number
US08785489B2

Reaction notes

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