Hydrochloric Acid → HCID 22262568, compound

HRID 1790378Notes

Reaction equation

HRID 1790378 reaction equation
[OH:1][CH2:2][C:3]([N:5]1[C:9]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[C:8]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][N:17]=2)[C:7]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[N:6]1)=[O:4].Cl>O1CCOCC1.CCOCC>[ClH:28].[OH:1][CH2:2][C:3]([N:5]1[C:9]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[C:8]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][N:17]=2)[C:7]([C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)=[N:6]1)=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22262569HCID 22262569, compound

Product 1

HCID 22262568HCID 22262568, compoundYield 190.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A 25 mL round bottom flask was charged with 65 mg (0.164 mmol) of N-(2-hydroxyacetyl)-5-(4-piperidyl)-4-(4-pyrimidyl)-3-(4-chlorophenyl)pyrazole and 2.5 mL of dioxane. To this suspension was added 0.082 mL of 4 N HCl in dioxane. The mixture was stirred for 2 hours. The mixture was diluted with 5 mL of Et2O and filtered. The solid was dried over solid CaSO4 under vacuum for 12 h to afford 68 mg of N-(2-hydroxyacetyl)-5-(4-piperidyl)-4-(4-pyrimidyl)-3-(4-chlorophenyl)pyrazole hydrochloride. 1H NMR (DMSO-d6) 9.18 (s, 1H), 8.63 (d, J=5.37 Hz, 1H), 7.40 (d, J=8.59 Hz, 2H), 7.33 (d, J=8.59 Hz, 2H), 7.15 (m, 1H), 4.40 (m, 1H), 4.06 (m, 2H), 3.72 (m, 1H), 3.33 (m, 1H), 2.97 (m, 1H), 2.62 (m, 1H), 1.83 (m, 2H), 1.64 (m, 2H); MS (M+H): 398.

Workup

  1. filtrationfiltered
  2. dry with materialThe solid was dried over solid CaSO4 under vacuum for 12 h

Sources & evidence

ORD record
ord-9256389df5634aa0b6a4f269a2a5d611
Source dataset
uspto-grants-2006_07
Patent number
US07071198B1

Reaction notes

Loading…