Potassium Carbonate → 1-Benzyl-2'-(4-phenoxyphenyl)-5',7'-dihydro-4'H-spiro[azetidine-3,6'-pyrazolo[1,5-a]pyrimidine]-3'-carbonitrile

HRID 64369Notes

Reaction equation

HRID 64369 reaction equation
[CH2:1]([N:8]1[CH2:11][C:10]([CH2:18]CS([O-])(=O)=O)([CH2:12]CS([O-])(=O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:24][C:25]1[NH:29][N:28]=[C:27]([C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:32][CH:31]=2)[C:26]=1[C:43]#[N:44].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([N:8]1[CH2:9][C:10]2([CH2:12][N:29]3[N:28]=[C:27]([C:30]4[CH:35]=[CH:34][C:33]([O:36][C:37]5[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=5)=[CH:32][CH:31]=4)[C:26]([C:43]#[N:44])=[C:25]3[NH:24][CH2:18]2)[CH2:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 131737216(1-Benzylazetidine-3,3-diyl)bis(methylene)dimethanesulfonateHCID 178509389HCID 178509389, compound

Product 1

HCID 1369280821-Benzyl-2'-(4-phenoxyphenyl)-5',7'-dihydro-4'H-spiro[azetidine-3,6'-pyrazolo[1,5-a]pyrimidine]-3'-carbonitrileYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (1-benzylazetidine-3,3-diyl)bis(methylene)dimethanesulfonate (300 mg, 0.83 mmol) in DMF (10 mL) was added 5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile (230 mg, 0.83 mmol) and K2CO3 (230 mg, 1.66 mmol). The mixture was stirred at 80° C. under N2 for 16 hr. The mixture was concentrated. The residue was washed with H2O (100 mL×2), dried and purified by pre-TLC (DCM/CH3OH=10/1) to afford 30 mg (10%) of desired product as a yellow liquid. MS (ESI) m/e [M+1]+ 447.9.

Workup

  1. concentrationThe mixture was concentrated
  2. washThe residue was washed with H2O (100 mL×2)
  3. customdried
  4. custompurified by pre-TLC (DCM/CH3OH=10/1)

Sources & evidence

ORD record
ord-c7fcfa7100f4462d8c53b393044f7c6a
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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