Dimethylformamide → HCID 21846079, compound

HRID 619170Notes

Reaction equation

HRID 619170 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=2)[C:9]#[N:10])[CH:5]=[CH:4][N:3]=[CH:2]1.[CH:14]1([N:19]2[C:23](N)=[C:22]([C:25]([NH2:27])=O)[C:21]([CH2:28][CH3:29])=[N:20]2)[CH2:18][CH2:17][CH2:16][CH2:15]1.[H-].[Na+].C[N:33](C=O)C>>[CH:14]1([N:19]2[C:23]3=[N:10][C:9]([C:8]4[CH:11]=[CH:12][CH:13]=[C:6]([N:1]5[CH:5]=[CH:4][N:3]=[CH:2]5)[CH:7]=4)=[N:27][C:25]([NH2:33])=[C:22]3[C:21]([CH2:28][CH3:29])=[N:20]2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydride2×HCID 49612723-(1H-imidazol-1-yl)benzonitrileHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 21846079HCID 21846079, compound

Procedure

To a mixture of 3-(1-imidazolyl)benzonitrile (3.16 g), 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (3.77 g, 16.98 mmol) and DMF (75 ml) was added NaH (0.78 g, 60% dispersion in mineral oil). The reaction mixture was stirred at room temperature for about 2 days, then additional nitrile (0.1 equivalents) and NaH (0.2 equivalents) were added and the mixture was stirred at room temperature overnight. The solvent was stripped, and the residue was partitioned between chloroform (150 ml) and water (350 ml). The layers were separated, the aqueous layer was extracted with chlorform (2×100 ml), and the organic layers were combined, washed with brine, dried over MgSO4, filtered and stripped. The product was dissolved in hot tert-butyldimethyl ether, filtered and stripped. The residue was treated with CH3CN and the solid which formed was collected by filtration to afford 2.10 g of 1-cyclopentyl-3-ethyl-6-[3-(1-imidazolyl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customthe residue was partitioned between chloroform (150 ml) and water (350 ml)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with chlorform (2×100 ml)
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. dissolutionThe product was dissolved in hot tert-butyldimethyl ether
  9. filtrationfiltered
  10. additionThe residue was treated with CH3CN
  11. customthe solid which formed
  12. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-14882b5aff8044f18c3ca37ae035a914
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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