Dimethylformamide → HCID 178462996, compound

HRID 1974251Notes

Reaction equation

HRID 1974251 reaction equation
C(O[C:4]([C:6]1[C:7](Cl)=[C:8]2[CH:14]=[N:13][N:12]([CH2:15][CH3:16])[C:9]2=[N:10][CH:11]=1)=[O:5])C.[NH2:18][C:19]1[NH:23][N:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.CN(C)C=O>O>[CH2:15]([N:12]1[C:9]2[N:10]=[CH:11][C:6]3[C:4](=[O:5])[N:23]4[N:22]=[CH:21][CH:20]=[C:19]4[NH:18][C:7]=3[C:8]=2[CH:14]=[N:13]1)[CH3:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 74561Pyrazol-3-ylamineHCID 10491120ethyl 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Product 1

HCID 178462996HCID 178462996, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

126 g. of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (0.5 mol.), 41.5 g. of 5-amino-pyrazole (0.5 mol.) and 50.6 g. of triethylamine (0.5 mol.) are heated at reflux temperature with stirring in 250 ml. of dimethylformamide for 16 hours. After cooling, about 300 ml. of water are added and the white precipitated product, 3-ethyl-3,11-dihydro-6H-pyrazolo[1,5-a]pyrazolo-[4',3':5,6]pyrido[4,3-d]pyrimidin-6-one is filtered off, yield 57.7 g. (45.4%); m.p. >300° (DMF).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. filtrationthe white precipitated product, 3-ethyl-3,11-dihydro-6H-pyrazolo[1,5-a]pyrazolo-[4',3':5,6]pyrido[4,3-d]pyrimidin-6-one is filtered off

Sources & evidence

ORD record
ord-f3b23b4c847145c49fc25cfb7250fcab
Source dataset
uspto-grants-1976_12
Patent number
US04000277

Reaction notes

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