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

HRID 37904Notes

Reaction equation

HRID 37904 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[CH:25]=[C:24]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[N:23]=[CH:22][N: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:25]=[C:24]([N:26]4[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]4)[N:23]=[CH:22][N:21]=3)[NH:2][CH:3]=2)[CH:11]=[N:12][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 441403054-Hydrazinyl-6-(piperidin-1-yl)pyrimidineHCID 68799628Ethyl 3-(dimethylamino)-2-(5-bromopyridin-3-yl)acrylate

Product 1

HCID 708727884-(5-Bromopyridin-3-yl)-2-(6-piperidin-1-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, 323 mg (1.7 mmol) of the compound from Example 8A and 58 mg (0.3 mmol) of p-toluenesulfonic acid are stirred in 2 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-40fc70cdf6ed40c89e12b09e7ec707d0
Source dataset
uspto-grants-2013_09
Patent number
US08524699B2

Reaction notes

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