Potassium Hydroxide → HCID 25003795, compound

HRID 1694389Notes

Reaction equation

HRID 1694389 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH:13][C:14]3([C:17]4[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=4)[CH2:16][CH2:15]3)=[O:12])[CH:10]=1)[N:7]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=1)[CH:6]=[CH:5]2.[OH-].[K+:39]>C1COCC1.CO>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH:13][C:14]3([C:17]4[CH:26]=[CH:25][C:20]([C:21]([O-:23])=[O:22])=[CH:19][CH:18]=4)[CH2:16][CH2:15]3)=[O:12])[CH:10]=1)[N:7]([CH2:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]([F:36])([F:35])[F:37])=[CH:32][CH:33]=1)[CH:6]=[CH:5]2.[K+:39]

Participants

4

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 58017569HCID 58017569, compound

Product 1

HCID 25003795HCID 25003795, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl 4-{1-[({5-fluoro-1-[4-(trifluoromethyl)benzyl]-1H-indol-7-yl}carbonyl)amino]cyclopropyl}benzoate (67 mg, 0.13 mmol) was dissolved in 1 ml THF/MeOH (1:1) and 0.5 ml 2N KOH. Then reaction mixture was stirred at RT for 18 h. The mixture was cooled and the solvents were evaporated under reduced pressure. 2N HCl was added (until pH=3) and the aqueous phase was extracted 3× with DCM. The combined organic layers were washed with water and brine, then dried over MgSO4, filtered and concentrated under reduced pressure. The residue was dissolved in 1 ml methanol and 1 eq of KOH (0.065 ml of 2N KOH) was added, the methanol was then evaporated under reduced pressure. The resulting solid was solubilised in water and the solution was lyophilized. 1H NMR (500 MHz, DMSO-d6): δ 9.15 (s, 1H), 7.70 (d, 2H), 7.55 (m, 4H), 7.15 (m, 1H), 7.05 (d, 2H), 6.90 (d, 2H), 6.65 (d, 1H), 5.65 (s, 2H), 1.70 (s, 2H), 1.05 (s, 2H), 0.80 (s, 2H).

Workup

  1. customThen reaction mixture
  2. temperatureThe mixture was cooled
  3. customthe solvents were evaporated under reduced pressure
  4. addition2N HCl was added (until pH=3)
  5. extractionthe aqueous phase was extracted 3× with DCM
  6. washThe combined organic layers were washed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. dissolutionThe residue was dissolved in 1 ml methanol
  11. customthe methanol was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-bb0038e4cfc74e0b83234629b3ca5ea7
Source dataset
uspto-grants-2012_04
Patent number
US08158671B2

Reaction notes

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