Sodium Hydroxide → HCID 11482191, compound

HRID 751696Notes

Reaction equation

HRID 751696 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][NH:6][C:7]([C:9]1[NH:18][C:12]2=[CH:13][N:14]=[C:15]([Cl:17])[CH:16]=[C:11]2[CH:10]=1)=[O:8])C.[OH-].[Na+]>C1COCC1>[Cl:17][C:15]1[CH:16]=[C:11]2[CH:10]=[C:9]([C:7]([NH:6][CH2:5][C:4]([OH:19])=[O:3])=[O:8])[NH:18][C:12]2=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11208307HCID 11208307, compound

Product 1

HCID 11482191HCID 11482191, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino] acetic acid ethyl ester (EXAMPLE 39, 500 mg, 1.8 mmol) in THF (30 mL) was added sodium hydroxide solution (1.8 mL, 2M, 3.6 mmol) and the reaction stirred at rt for 4 h. The solvent was removed in vacuo and the solid partitioned between hydrochloric acid (1M, 100 mL) and ethyl acetate (2×100 mL). The aqueous layer was concentrated in vacuo and the solid residue suspended in water (10 mL), filtered and dried to give the title compound as an off-white solid. δH (d6 DMSO): 3.97 (2H, d), 7.18 (1H, s), 7.76 (1H, s), 8.57 (1H, s), 9.17 (1H, t), 12.32 (1H, s); m/z (ES+)=254 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe solid partitioned between hydrochloric acid (1M, 100 mL) and ethyl acetate (2×100 mL)
  3. concentrationThe aqueous layer was concentrated in vacuo
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-752c961194af47c78196c2c411507624
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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