Hydrochloric Acid → HCID 58087848, compound

HRID 1098424Notes

Reaction equation

HRID 1098424 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:13]([C:14](=[O:30])[C:15]3[C:20]([F:21])=[CH:19][CH:18]=[C:17]([NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])[C:16]=3[F:29])=[CH:12][NH:11][C:8]2=[N:9][CH:10]=1)=[O:4].O.[OH-].[Li+].Cl>O1CCCC1>[F:29][C:16]1[C:17]([NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])=[CH:18][CH:19]=[C:20]([F:21])[C:15]=1[C:14]([C:13]1[C:7]2[C:8](=[N:9][CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=2)[NH:11][CH:12]=1)=[O:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 3939Lithium HydroxideHCID 58086267HCID 58086267, compound

Product 1

HCID 58087848HCID 58087848, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3-[2,6-difluoro-3-(propane-1-sulfonylamino)-benzoyl]-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid methyl ester (P-1552, 80.0 mg, 0.18 mmol) in tetrahydrofuran (10.0 mL) were added water (3.0 mL) and lithium hydroxide (82 mg, 3.4 mmol). The reaction was stirred at room temperature overnight. The reaction was poured into water, acidified with 1 N HCl to pH around 1, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, concentrated, and washed with ethyl acetate to give an off-white solid (P-1559, 60 mg, 77%) MS (ESI) [M+H+]+=424.2.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washwashed with ethyl acetate
  6. customto give an off-white solid (P-1559, 60 mg, 77%)

Sources & evidence

ORD record
ord-6eb96415325e4a829fbe69adeb709e39
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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