Potassium Hydroxide → HCID 178451814, compound

HRID 1888226Notes

Reaction equation

HRID 1888226 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][N:9]=[C:8]2[CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)#[N:2].[OH-:31].[K+]>C(O)CCC>[NH2:2][C:1]([C:3]1[CH:4]=[C:5]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][N:9]=[C:8]2[CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:31]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178451812HCID 178451812, compound2×

Product 1

HCID 178451814HCID 178451814, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 1,1-dimethylethyl 4-(7-cyano-5-phenyl-1H-indazol-3-yl)-1-piperidine-carboxylate (Intermediate 4) (1.1 g, 2.7 mmols), and potassium hydroxide (1.53 g, 27.3 mmols) in n-butanol (100 mL) was heated at 85° C. for 2-3 days then at reflux overnight. The solution was cooled and the solvent removed in vacuo. The resulting residue was purified via silica gel chromatography eluting with 50% ethyl acetate/pentane, 100% ethyl acetate, and 30% methanol/ethyl acetate to give 0.68 g of a yellow solid. LC/MS M+H 421

Workup

  1. temperatureat reflux overnight
  2. temperatureThe solution was cooled
  3. customthe solvent removed in vacuo
  4. customThe resulting residue was purified via silica gel chromatography
  5. washeluting with 50% ethyl acetate/pentane, 100% ethyl acetate, and 30% methanol/ethyl acetate

Sources & evidence

ORD record
ord-84883ed69c584e8ab7e6afdce2e3946a
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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