Potassium Carbonate → 5-[2-(4,4-difluoropiperidin-1-yl)ethoxy]-2-methyl-3-{4-phenyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-1,3-thiazol-2-yl}pyrazolo[1,5-a]pyridine

HRID 2282235Notes

Reaction equation

HRID 2282235 reaction equation
[CH3:1][C:2]1[C:11]([C:12]2[S:13][C:14]([C:23]3[N:27]=[CH:26][N:25]([CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][O:29]4)[N:24]=3)=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:16]=2)=[C:5]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][N:4]2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:41][CH2:42][N:43]1[CH2:48][CH2:47][C:46]([F:50])([F:49])[CH2:45][CH2:44]1>>[F:49][C:46]1([F:50])[CH2:47][CH2:48][N:43]([CH2:42][CH2:41][O:10][C:7]2[CH:8]=[CH:9][N:4]3[N:3]=[C:2]([CH3:1])[C:11]([C:12]4[S:13][C:14]([C:23]5[N:27]=[CH:26][N:25]([CH:28]6[CH2:33][CH2:32][CH2:31][CH2:30][O:29]6)[N:24]=5)=[C:15]([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)[N:16]=4)=[C:5]3[CH:6]=2)[CH2:44][CH2:45]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 179639191-(2-Chloroethyl)-4,4-difluoropiperidineHCID 178433751HCID 178433751, compound

Product 1

HCID 668554075-[2-(4,4-difluoropiperidin-1-yl)ethoxy]-2-methyl-3-{4-phenyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-1,3-thiazol-2-yl}pyrazolo[1,5-a]pyridineYield 91%

Procedure

The title compound has been prepared according to the similar manner described in 85-B (ii) using 2-methyl-3-{4-phenyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-1,3-thiazol-2-yl}pyrazolo[1,5-a]pyridin-5-ol (100 mg, 0.218 mmol) obtained in Example 31-B-(i), potassium carbonate (75.3 mg, 0.545 mmol) and 1-(2-chloroethyl)-4,4-difluoropiperidine (80.0 mg, 0.436 mmol) obtained above. The crude product was purified by basic silica gel column chromatography (EtOAc/hexane=20/80→50/50) to give pure title compound (120 mg, 91%) as a colorless solid.

Workup

  1. customobtained above
  2. customThe crude product was purified by basic silica gel column chromatography (EtOAc/hexane=20/80→50/50)

Sources & evidence

ORD record
ord-d18a4804a099489b8fa83ca12cfcb7d9
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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