Hydrochloric Acid → 4-(5-Bromopyridin-3-yl)-2-(6-morpholin-4-ylpyrimidin-4-yl)-1,2-dihydro-3H-pyrazol-3-one hydrochloride

HRID 37905Notes

Reaction equation

HRID 37905 reaction equation
C[N:2](C)[CH:3]=[C:4]([C:10]1[CH:11]=[N:12][CH:13]=[C:14]([Br:16])[CH:15]=1)[C:5]([O:7]CC)=O.[NH:18]([C:20]1[N:25]=[CH:24][N:23]=[C:22]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH:21]=1)N.C1(C)C=CC(S(O)(=O)=O)=CC=1.[ClH:43]>C(O)C.O1CCOCC1>[ClH:43].[Br:16][C:14]1[CH:15]=[C:10]([C:4]2[C:5](=[O:7])[N:18]([C:20]3[CH:21]=[C:22]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[N:23]=[CH:24][N:25]=3)[NH:2][CH:3]=2)[CH:11]=[N:12][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 13393622(6-Morpholin-4-ylpyrimidin-4-yl)hydrazineHCID 68799628Ethyl 3-(dimethylamino)-2-(5-bromopyridin-3-yl)acrylate

Product 1

HCID 708726644-(5-Bromopyridin-3-yl)-2-(6-morpholin-4-ylpyrimidin-4-yl)-1,2-dihydro-3H-pyrazol-3-one hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

At 100° C., 500 mg (1.7 mmol) of the compound from Example 11A, 326 mg (1.7 mmol) of the compound from Example 9A and 58 mg (0.3 mmol) of p-toluenesulfonic acid are stirred in 4 ml of ethanol for 16 h. After cooling to RT, 0.5 ml of a 4 N solution of hydrogen chloride in dioxane is added, and the mixture is stirred at RT for 30 min. The precipitate is filtered off, washed first with ethanol and then with diethyl ether and dried under reduced pressure.

Workup

  1. filtrationThe precipitate is filtered off
  2. washwashed first with ethanol
  3. dry with materialwith diethyl ether and dried under reduced pressure

Sources & evidence

ORD record
ord-5b72c88a36a143439e8ea50a528703bc
Source dataset
uspto-grants-2013_09
Patent number
US08524699B2

Reaction notes

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