Water → HCID 71504801, compound

HRID 2274947Notes

Reaction equation

HRID 2274947 reaction equation
[F:1][C:2]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[C:13]2[CH2:12][CH2:11][NH:10][CH2:9][C:8]=2[C:7]([C:14]2[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=2)[C:17]#[N:18])=[N:6]1.C([O-])([O-])=O.[K+].[K+].[C:33](Cl)(=[O:37])[CH:34]([CH3:36])[CH3:35].O>CC#N>[F:1][C:2]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[C:13]2[CH2:12][CH2:11][N:10]([C:33](=[O:37])[CH:34]([CH3:36])[CH3:35])[CH2:9][C:8]=2[C:7]([C:14]2[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=2)[C:17]#[N:18])=[N:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 62325Isobutyryl chlorideHCID 89443793HCID 89443793, compound

Product 1

HCID 71504801HCID 71504801, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-[1-(2,4-Difluoro-benzyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile (7c) (0.057 g, 0.163 mmol), K2CO3 (45 mg, 0.327 mmol) and isobutyryl chloride (21 mg, 0.196 mmol) in dry CH3CN (1.5 ml) was stirred at 60° C. for 1 h. Water was added, the solution was extracted 3 times with CH2Cl2, the combined organic layers were washed once with brine, dried over Na2SO4, filtrated and the residue was purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid) to give 48 mg of 3-[1-(2,4-Difluoro-benzyl)-5-isobutyryl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile (8b).

Workup

  1. extractionthe solution was extracted 3 times with CH2Cl2
  2. washthe combined organic layers were washed once with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltrated
  5. customthe residue was purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-fec1fe4c3c8e4498810d8be55644dc2d
Source dataset
uspto-grants-2015_09
Patent number
US09127001B2

Reaction notes

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