Dimethylformamide → HCID 178459974, compound

HRID 1762103Notes

Reaction equation

HRID 1762103 reaction equation
C(N(CC)CC)C.CN(C)C=O.[O:13]1[CH2:18][CH2:17][N:16]([C:19]2[NH:20][N:21]3[CH2:26][C:25]4[CH2:27][NH:28][CH2:29][C:30](=[O:31])[C:24]=4[N:23]=[C:22]3[N:32]=2)[CH2:15][CH2:14]1.[C:33](Cl)(=[O:36])[CH2:34][CH3:35]>O.CN(C)P(=O)(N(C)C)N(C)C>[O:13]1[CH2:14][CH2:15][N:16]([C:19]2[NH:20][N:21]3[CH2:26][C:25]4[CH2:27][N:28]([C:33](=[O:36])[CH2:34][CH3:35])[CH2:29][C:30](=[O:31])[C:24]=4[N:23]=[C:22]3[N:32]=2)[CH2:17][CH2:18]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 178516740HCID 178516740, compound

Product 1

HCID 178459974HCID 178459974, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

To a mixture of 0.50 g (0.005 mole, 0.69 ml) of triethyl amine, 4 ml of dimethyl formamide, 1 ml of hexamethyl phosphoric triamide and 0.828 g (0.003 mole) of 2-morpholino-6,7,8,9-tetrahydro-pyrido[4,3-d]-1,2,4-triazolo[1,5-a]-pyrimidine-5(10H)-one are added. To the mixture 0.46 g (0.005 mole, 0.43 ml) of propionyl chloride are added under stirring and the reaction mixture is first stirred at 25° C. for six hours and a half and then allowed to stand at room temperature for 16 hours. After addition of 25 ml of water the precipitated crystals are filtered and washed with acetone. The solid is dissolved in 6 ml of hot dimethyl formamide and precipitated by adding 15 ml of acetonitrile. Thus 0.63 g of the desired compound is obtained, yield 63%, m.p.: 278°-280° C.

Workup

  1. additionare added
  2. stirringthe reaction mixture is first stirred at 25° C. for six hours
  3. filtrationare filtered
  4. washwashed with acetone
  5. dissolutionThe solid is dissolved in 6 ml of hot dimethyl formamide
  6. customprecipitated
  7. additionby adding 15 ml of acetonitrile

Sources & evidence

ORD record
ord-43a8f399ed2845278ee8f47c1e6974e0
Source dataset
uspto-grants-1989_05
Patent number
US04831029

Reaction notes

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