Hydrochloric Acid → HCID 178423772, compound

HRID 1188147Notes

Reaction equation

HRID 1188147 reaction equation
O1CCCCC1[N:7]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[CH:10][C:9]([C:19]([NH:21][C:22]2[N:26](C3CCCCO3)[N:25]=[C:24]([C:33](=O)[NH:34][C:35]3[CH:39]=[C:38]([C:40]4[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=4)[N:37](C4CCCCO4)[N:36]=3)[CH:23]=2)=O)=[N:8]1.CO.Cl>C1COCC1>[C:43]1([CH3:46])[CH:42]=[CH:41][C:40]([C:38]2[NH:37][N:36]=[C:35]([NH:34][CH2:33][C:24]3[CH:23]=[C:22]([NH:21][CH2:19][C:9]4[CH:10]=[C:11]([C:12]5[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=5)[NH:7][N:8]=4)[NH:26][N:25]=3)[CH:39]=2)=[CH:45][CH:44]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 59408779HCID 59408779, compound

Product 1

HCID 178423772HCID 178423772, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-(Tetrahydro-2H-pyran-2-yl)-N-(1-(tetrahydro-2H-pyran-2-yl)-3-(1-(tetrahydro-2H-pyran-2-yl)-5-p-tolyl-1H-pyrazol-3-ylcarbamoyl)-1H-pyrazol-5-yl)-5-p-tolyl-1H-pyrazole-3-carboxamide (28 mg, 0.04 mmol) was suspended in anhydrous THF (500 μL) and borane dimethylsulfide complex (26 μL, 0.27 mmol) was added dropwise. The reaction mixture was stirred under reflux for 16 hrs. The reaction mixture was then cooled down to 0° C. and MeOH (50 μL) was added and the mixture was stirred for 10 min. Concentrated hydrochloric acid (12 N) was added until pH<2 was obtained The resulting mixture was stirred at 50° C. for 16 hrs. The mixture was cooled to room temperature and the solvent was evaporated. The residue was resuspended in THF and the precipitate was filtrated and washed with cold THF. 5-p-Tolyl-N-((5-((5-p-tolyl-1H-pyrazol-3-yl)methylamino)-1H-pyrazol-3-yl)methyl)-1H-pyrazol-3-amine was obtained as a white solid.

Workup

  1. additionborane dimethylsulfide complex (26 μL, 0.27 mmol) was added dropwise
  2. temperatureunder reflux for 16 hrs
  3. stirringthe mixture was stirred for 10 min
  4. customwas obtained The resulting mixture
  5. stirringwas stirred at 50° C. for 16 hrs
  6. temperatureThe mixture was cooled to room temperature
  7. customthe solvent was evaporated
  8. filtrationthe precipitate was filtrated
  9. washwashed with cold THF

Sources & evidence

ORD record
ord-44a7aff724a649e4a45669809bea8dae
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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