Hydrochloric Acid → HCID 67021571, compound

HRID 1660990Notes

Reaction equation

HRID 1660990 reaction equation
[Li+].[OH-].C([O:5][C:6]([CH:8]1[C:16]2[C:11](=[CH:12][C:13]([N:17]3[C:21]4=[N:22][CH:23]=[CH:24][CH:25]=[C:20]4[N:19]=[CH:18]3)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])C.[OH-].[Na+].Cl>C1COCC1.O.CCO>[N:19]1[C:20]2[C:21](=[N:22][CH:23]=[CH:24][CH:25]=2)[N:17]([C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[CH:8]([C:6]([OH:7])=[O:5])[CH2:9][CH2:10]3)[CH:18]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 131729211HCID 131729211, compound

Product 1

HCID 67021571HCID 67021571, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1M LiOH (1.8 mL, 1.8 mmol) is added to a solution of (R/S)-5-imidazo[4,5-b]pyridine-3-yl-indan-1-carboxylic acid ethyl ester (550 mg, 1.8 mmol) in THF (2 mL). EtOH (2 mL) is added and after 10 min, 1N NaOH (2.5 mL) is added. The mixture is stirred at rt for 1.5 h and then acidified with 1M HCl. Water is added to the reaction mixture and the compound extracted with EtOAc. The organic layers are combined and washed with brine, dried with MgSO4, filtered and concentrated to give (R/S)-5-imidazo[4,5-b]pyridine-3-yl-indan-1-carboxylic acid as a white solid. Title compound: ES-MS: 280.09 [M+H]+; tR=1.0 min (System 2).

Workup

  1. extractionthe compound extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-395b2690b9ca472eb9285796d3afa7d7
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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