Ammonia → HCID 59278478, compound

HRID 559637Notes

Reaction equation

HRID 559637 reaction equation
C([O:3][C:4](=O)[CH2:5][S:6]([C:9]1[CH:14]=[C:13]([CH2:15][NH:16][C:17]([C:19]2[C:20]3[CH:27]=[N:26][N:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[C:21]=3[CH:22]=[N:23][CH:24]=2)=[O:18])[CH:12]=[CH:11][N:10]=1)(=[O:8])=[O:7])C.[NH3:36].CO>>[C:4]([CH2:5][S:6]([C:9]1[CH:14]=[C:13]([CH2:15][NH:16][C:17]([C:19]2[C:20]3[CH:27]=[N:26][N:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[C:21]=3[CH:22]=[N:23][CH:24]=2)=[O:18])[CH:12]=[CH:11][N:10]=1)(=[O:8])=[O:7])(=[O:3])[NH2:36]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 45137106HCID 45137106, compound

Product 1

HCID 59278478HCID 59278478, compound

Procedure

In a sealed tube, a solution of [4-({[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-methyl)-pyridine-2-sulfonyl]-acetic acid ethyl ester (40 mg, 0.08 mmol) in a 7 N solution of ammonia in methanol (345 μL, 2.41 mmol) was warmed at 100° C. After 6 hours, the mixture was cooled to room temperature, and the resulting precipitate collected by filtration. The solid was purified by reversed-phase HPLC (C18 column, flow rate=25 mL/minute) using a 20 minute gradient of 5-95% acetonitrile (0.1% TFA) in water (0.1% TFA). Desired fractions from the column were combined and neutralized with saturated aqueous sodium bicarbonate, concentrated and extracted with a 10% solution of methanol in dichloromethane (3×30 mL). The combined organic layer were dried over magnesium sulfate, filtered and concentrated. The solid was triturated with methanol (3×1 mL), filtered and dried to afford the title compound.

Workup

  1. filtrationthe resulting precipitate collected by filtration
  2. customThe solid was purified by reversed-phase HPLC (C18 column, flow rate=25 mL/minute)
  3. waitusing a 20 minute
  4. concentrationconcentrated
  5. extractionextracted with a 10% solution of methanol in dichloromethane (3×30 mL)
  6. dry with materialThe combined organic layer were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe solid was triturated with methanol (3×1 mL)
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-4bcbd89768964e2785714861a17e7cd3
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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