Water → HCID 53357944, compound

HRID 1500771Notes

Reaction equation

HRID 1500771 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]3[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][C:12]=23)[CH:5]=[CH:4][CH:3]=1.[CH:19]1([CH2:25][NH2:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C(N(CC)CC)C.O>CS(C)=O>[CH:19]1([CH2:25][NH:26][C:2]2[N:7]=[C:6]([C:8]3[CH:9]=[N:10][N:11]4[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][C:12]=34)[CH:5]=[CH:4][CH:3]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 76688CyclohexanemethylamineHCID 86691789HCID 86691789, compound

Product 1

HCID 53357944HCID 53357944, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3-(6-chloropyridin-2-yl)pyrazolo[1,5-a]pyridine-5-carbonitrile (Preparation 6, 30 mg, 0.12 mmol), cyclohexylmethanamine (46 μL, 0.35 mmol) and triethylamine (50 μL, 0.36 mmol) in dimethylsulfoxide (0.5 mL) was heated at 140° C. for 20 hours. The mixture was then cooled, water was added and the resultant precipitate was filtered and dried in vacuo. Purification of the solid by flash chromatography (dichloromethane to 150:1 dichloromethane/methanol) gave the title compound (13 mg, 33%) as a yellow foam.

Workup

  1. temperatureThe mixture was then cooled
  2. filtrationthe resultant precipitate was filtered
  3. customdried in vacuo
  4. customPurification of the solid by flash chromatography (dichloromethane to 150:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-76f9428c3b68493d9f53e3d287a766c6
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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