p-Toluenesulfonic acid monohydrate → HCID 178427649, compound

HRID 1530070Notes

Reaction equation

HRID 1530070 reaction equation
[CH3:1][C:2]1[C:20]([C:21]2[S:22][C:23]([C:32]3[N:36]=[CH:35][NH:34][N:33]=3)=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:25]=2)=[C:5]2[CH:6]=[C:7]([O:10][CH2:11][CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH:8]=[CH:9][N:4]2[N:3]=1.O.[C:38]1([CH3:48])[CH:43]=[CH:42][C:41]([S:44]([OH:47])(=[O:46])=[O:45])=[CH:40][CH:39]=1>CCO>[C:38]1([CH3:48])[CH:39]=[CH:40][C:41]([S:44]([OH:47])(=[O:45])=[O:46])=[CH:42][CH:43]=1.[CH3:1][C:2]1[C:20]([C:21]2[S:22][C:23]([C:32]3[N:36]=[CH:35][NH:34][N:33]=3)=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:25]=2)=[C:5]2[CH:6]=[C:7]([O:10][CH2:11][CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[CH:8]=[CH:9][N:4]2[N:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 178433756HCID 178433756, compound

Product 1

HCID 178427649HCID 178427649, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of 2-methyl-5-(3-morpholin-4-ylpropoxy)-3-[4-phenyl-5-(1H-1,2,4-triazol-3-yl)-1,3-thiazol-2-yl]pyrazolo[1,5-a]pyridine (85.8 mg, 0.171 mmol) obtained above in EtOH (10 mL), was added a solution of p-toluene sulfonic acid monohydrate (71.6 mg, 0.376 mmol) in EtOH (2 mL) and then resulting mixture was concentrated under reduced pressure. The residue was crystallized from EtOH (2 mL) and EtOAc (6 mL) to obtain title compound (106 mg, 92%) as a pale yellow solid.

Workup

  1. customresulting mixture
  2. concentrationwas concentrated under reduced pressure
  3. customThe residue was crystallized from EtOH (2 mL) and EtOAc (6 mL)

Sources & evidence

ORD record
ord-0dcf85b45d84465dbe7991d7ee1b81ee
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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