Potassium Hydroxide → HCID 178477693, compound

HRID 1888255Notes

Reaction equation

HRID 1888255 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:28]#[N:29])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[F:27])[CH:19]=3)[NH:14][N:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].[OH-:30].[K+]>CC(O)(C)C>[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:28]([NH2:29])=[O:30])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[F:27])[CH:19]=3)[NH:14][N:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178477689HCID 178477689, compound2×

Product 1

HCID 178477693HCID 178477693, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

The mixture of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(2-fluorophenyl)-1H-indazole-7-carbonitrile (Intermediate 12) (0.102 mmols) and potassium hydroxide (26 mg, 0.51 mmol) in 2-methyl-2-propanol (4 mL) was heated overnight. The reaction mixture was concentrated. The residue was purified by using a Gilson semi-preparative HPLC system, eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) pumped at 25 mL/min to afford the title compound (11 mg, 25% for 2 steps)

Workup

  1. temperaturewas heated overnight
  2. concentrationThe reaction mixture was concentrated
  3. customThe residue was purified
  4. washeluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-371de66e46da49e19e153e6ff7f034b9
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

Loading…