Potassium Hydroxide → HCID 178477697, compound

HRID 1888254Notes

Reaction equation

HRID 1888254 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][C:24]([F:27])=[CH:23][CH:22]=4)[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:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=4)[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 178477690HCID 178477690, compound2×

Product 1

HCID 178477697HCID 178477697, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

The mixture of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(4-fluorophenyl)-1H-indazole-7-carbonitrile (Intermediate 11) (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 and purified by using a Gilson semi-preparative HPLC system with a YMC ODS-A (C-18) column 50 mm by 20 mm ID, eluting with 10% B to 70% B in 3.2 min, hold for 1 min where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) pumped at 25 mL/min to afford the title compound (21 mg, 48% for 2 steps)

Workup

  1. temperaturewas heated overnight
  2. concentrationThe reaction mixture was concentrated
  3. custompurified
  4. washeluting with 10% B to 70% B in 3.2 min

Sources & evidence

ORD record
ord-876669da277c4115b615bc4fd291af2d
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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