Hydrochloric Acid → HCID 25000164, compound

HRID 249820Notes

Reaction equation

HRID 249820 reaction equation
C[O:2][C:3](=[O:39])[CH2:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:14]([C:15](=[O:38])[C:16]3[C:21]([F:22])=[CH:20][CH:19]=[C:18]([NH:23][S:24]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=4)(=[O:26])=[O:25])[C:17]=3[F:37])=[CH:13][NH:12][C:9]2=[N:10][CH:11]=1.[OH-].[Li+].Cl>O1CCCC1>[F:37][C:17]1[C:18]([NH:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[CH:19][CH:20]=[C:21]([F:22])[C:16]=1[C:15]([C:14]1[C:8]2[C:9](=[N:10][CH:11]=[C:6]([CH2:5][CH2:4][C:3]([OH:39])=[O:2])[CH:7]=2)[NH:12][CH:13]=1)=[O:38]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 25000163HCID 25000163, compound

Product 1

HCID 25000164HCID 25000164, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To 3-{3-[2,6-difluoro-3-(4-trifluoromethyl-benzenesulfonylamino)-benzoyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-propionic acid methyl ester (P-0033, 215 mg, 0.38 mmol) dissolved in tetrahydrofuran (30 mL) was added 1 N lithium hydroxide solution (15 mL). The mixture was heated at 50° C. for 2 hrs, then acidified to pH˜1-2 with 6 N HCl and extracted with ethyl acetate. The organic layer was washed with water and brine dried over anhydrous magnesium sulfate, filtered and concentrated to provide an off-white solid (P-0034, 202 mg, 96%). MS(ESI) [M+H+]+=554.0.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide an off-white solid (P-0034, 202 mg, 96%)

Sources & evidence

ORD record
ord-09dd1c04672f4309a86b4fa76e245280
Source dataset
uspto-grants-2011_01
Patent number
US07863289B2

Reaction notes

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