Potassium Carbonate → tert-butyl 4-[(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-yl)oxy]piperidine-1-carboxylate

HRID 2282246Notes

Reaction equation

HRID 2282246 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:34](=[O:37])([O-])[O-:35].[K+].[K+].CS(O[CH:45]1[CH2:50][CH2:49][N:48](OC(OC(C)(C)C)=O)[CH2:47][CH2:46]1)(=O)=O>>[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]([O:10][CH:45]3[CH2:50][CH2:49][N:48]([C:34]([O:35][C:11]([CH3:12])([CH3:2])[CH3:5])=[O:37])[CH2:47][CH2:46]3)[CH:8]=[CH:9][N:4]2[N:3]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 866496051-[(Tert-butoxycarbonyl)oxy]piperidin-4-yl methanesulfonateHCID 178433751HCID 178433751, compound

Product 1

HCID 66854819tert-butyl 4-[(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-yl)oxy]piperidine-1-carboxylateYield 183.5%

Procedure

The title compound has been prepared according to the similar manner described in 85-B (ii) from 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 (490 mg, 1.07 mmol) obtained in Example 31-B-(i), potassium carbonate (444 mg, 3.21 mmol) and 1-[(tert-butoxycarbonyl)oxy]piperidin-4-yl methanesulfonate (897 mg, 3.21 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 (630 mg, 92%) as a pale yellow 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-b5fb66075da440f286e3f00ac52ce6d4
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

Loading…