Hydrochloric Acid → HCID 58087848, compound

HRID 250606Notes

Reaction equation

HRID 250606 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-562b38abc0b6460da43866efc07202c8
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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