Dimethylformamide diethylacetal → N'-[3-(morpholin-4-yl)-4-cyano-1H-pyrazol-5-yl]-N,N-dimethyl-formamidine

HRID 1068890

Reaction equation

HRID 1068890 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([N:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[C:3]=1[C:13]#[N:14].C(O[CH:18](OCC)[N:19]([CH3:21])[CH3:20])C>C1(C)C=CC=CC=1>[N:7]1([C:4]2[C:3]([C:13]#[N:14])=[C:2]([N:1]=[CH:18][N:19]([CH3:21])[CH3:20])[NH:6][N:5]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 49626575-amino-3-(morpholin-4-yl)-1H-pyrazole-4-carbonitrile

Product 1

HCID 54020168N'-[3-(morpholin-4-yl)-4-cyano-1H-pyrazol-5-yl]-N,N-dimethyl-formamidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, a suspension of 4.00 g (20.7 mmol) of 5-amino-3-(morpholin-4-yl)-1H-pyrazole-4-carbonitrile in 85 ml of toluene is boiled under reflux for 5 hours with 4.17 ml (97%; 23.6 mmol) of N,N-dimethylformamide diethyl acetal, during which the solid dissolves. Cooling to RT (→crystallization), filtration with suction an d washing with toluene and hexane yield N′-[3-(morpholin-4-yl)-4-cyano-1H-pyrazol-5-yl]-N,N-dimethyl-formamidine; m.p. 182-183° C.; TLC: Rf=0.20 (ethyl acetate).

Workup

  1. dissolutiondissolves
  2. filtration(→crystallization), filtration with suction
  3. washan d washing with toluene and hexane

Sources & evidence

ORD record
ord-2267d8654dfb42d1ab8ac664cd0cce9e
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Linked notes

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