Dimethylformamide → HCID 67946498, compound

HRID 973425Notes

Reaction equation

HRID 973425 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[C:7](=[O:17])[N:6]([CH3:18])[CH2:5]1.[C:19]1([N:25]2[C:29]3([CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[C:28](=[O:35])[NH:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:36]([O-])(O)=O.[Na+].CN(C=O)C>O>[CH2:28]([O:35][C:7](=[O:17])[CH3:36])[CH3:29].[CH3:18][N:6]1[CH2:5][CH:4]([CH2:3][CH2:2][N:32]2[CH2:31][CH2:30][C:29]3([N:25]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:26][NH:27][C:28]3=[O:35])[CH2:34][CH2:33]2)[C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[C:7]1=[O:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 516892Sodium BicarbonateHCID 199898454-(2-Chloroethyl)-3,4-dihydro-2-methylpyrimido[1,6-a]benzimidazol-1(2H)-one

Product 1

HCID 67946498HCID 67946498, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.0 g (0.015 mol) of 4-(2-chloroethyl)-3,4-dihydro-2-methylpyrimido[1,6-a]benzimidazole-1(2H)-one, 3.46 g (0.015 mol) of 1-phenyl-1,3,8-triazaspiro[4,5]-decan-4-one, 9 g of NaHCO3, 0.5 g of Kl, and 35 mL of DMF was heated on a steam cone for 24 h. The reaction mixture was poured into 500 mL of H2O and extracted with 3×100 mL of CH2Cl2. The combined organic extracts were washed with 2×100 mL of H2O, dried (NaSO4), filtered and concentrated by rotary evaporation. The residue was purified by preparative HPLC using acetone and the eluent and silica gel as the stationary phase. Like fractions were combined and concentrated by rotary evaporation to a glass which crystallized upon treatment with ethyl acetate to give 4.3 g (52%) of analytically pure material, mp 173°-75° C.

Workup

  1. temperaturewas heated on a steam cone for 24 h
  2. extractionextracted with 3×100 mL of CH2Cl2
  3. washThe combined organic extracts were washed with 2×100 mL of H2O
  4. dry with materialdried (NaSO4)
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation
  7. customThe residue was purified by preparative HPLC
  8. concentrationconcentrated by rotary evaporation to a glass which
  9. customcrystallized upon treatment with ethyl acetate
  10. customto give 4.3 g (52%) of analytically pure material, mp 173°-75° C.

Sources & evidence

ORD record
ord-11e0f0bd9ecb4a3ab34b31e6aaa58080
Source dataset
uspto-grants-1991_11
Patent number
US05063228

Reaction notes

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