Potassium Carbonate → 2-{6-[3-(Dimethylamino)azetidin-1-yl]pyrimidin-4-yl}-4-(1H-1,2,3-triazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one dihydrochloride

HRID 562468Notes

Reaction equation

HRID 562468 reaction equation
[ClH:1].Cl.[CH3:3][N:4]([CH3:9])[CH:5]1[CH2:8][NH:7][CH2:6]1.Cl.[Cl:11][C:12]1[N:17]=[CH:16][N:15]=[C:14]([N:18]2[C:22](=[O:23])[C:21]([N:24]3[CH:28]=[CH:27][N:26]=[N:25]3)=[CH:20][NH:19]2)[CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[ClH:11].[ClH:1].[CH3:3][N:4]([CH3:9])[CH:5]1[CH2:8][N:7]([C:12]2[N:17]=[CH:16][N:15]=[C:14]([N:18]3[C:22](=[O:23])[C:21]([N:24]4[CH:28]=[CH:27][N:26]=[N:25]4)=[CH:20][NH:19]3)[CH:13]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22121220N,N-dimethylazetidin-3-amine dihydrochlorideHCID 866352542-(6-Chloropyrimidin-4-yl)-4-(1H-1,2,3-triazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one hydrochloride

Product 1

HCID 444646132-{6-[3-(Dimethylamino)azetidin-1-yl]pyrimidin-4-yl}-4-(1H-1,2,3-triazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one dihydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

271 mg (1.5 mmol) of N,N-dimethylazetidine-3-amine dihydrochloride, 400 mg (1.5 mmol) of the compound from Example 12A and 847 mg (6.1 mmol) of potassium carbonate are suspended in 8 ml of N,N-dimethylformamide and stirred at 100° C. for 16 h. The reaction mixture is concentrated under reduced pressure and purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% strength trifluoroacetic acid). Further purification is carried out by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% strength formic acid). 2 ml of 1 N hydrochloric acid is added to the product-containing fractions, and the mixture is stirred at RT for 1 h. The solid is filtered off and dried under high vacuum. Yield: 62 mg (17% of theory)

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. custompurified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% strength trifluoroacetic acid)
  3. customFurther purification
  4. additionis carried out by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% strength formic acid)
  5. addition2 ml of 1 N hydrochloric acid is added to the product-containing fractions
  6. stirringthe mixture is stirred at RT for 1 h
  7. filtrationThe solid is filtered off
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-6fb4d86593e54669914fe6935acce6e0
Source dataset
uspto-grants-2011_11
Patent number
US08067407B2

Reaction notes

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