5-Amino-4-cyanopyrazole → HCID 178510454, compound

HRID 460684

Reaction equation

HRID 460684 reaction equation
CO[C:3](=[O:23])[C:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)=[CH:5][N:6]([CH3:8])C.[NH2:24][C:25]1[NH:29][N:28]=[CH:27][C:26]=1C#N>C(O)(=O)C.C(OCC)(=O)C.CCCCCC>[CH2:16]([O:15][C:12]1[CH:11]=[CH:10][C:9]([C:4]2[C:3](=[O:23])[N:29]3[N:28]=[CH:27][C:26]([C:25]#[N:24])=[C:8]3[NH:6][CH:5]=2)=[CH:14][CH:13]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 2

HCID 855155-Amino-4-cyanopyrazoleHCID 69154646Methyl 2-[4-(benzyloxy)phenyl]-3-dimethylamino-2-propenoate

Product 1

HCID 178510454HCID 178510454, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.21 g (3.9 mmol) of 2-(4-benzyloxy-phenyl)-3-dimethylamino-acrylic acid methyl ester and 0.422 g (3.9 mmol) of 5-amino-1H-pyrazole-4-carbonitrile in 5 mL of acetic acid (HOAc) was heated at reflux overnight, during which time a precipitate formed. The reaction mixture was cooled to rt, diluted with 20% ethyl acetate in hexane solution, and filtered to give 0.86 g (65% over 2 steps) of 6-(4-benzyloxy-phenyl)-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-3-carbonitrile as a tan colored solid as indicated by 1H NMR; LC-MS—calcd for C20H14N4O2 [M++H]+: 343.11, found: 343.1.

Workup

  1. temperatureat reflux overnight, during which time a precipitate
  2. customformed
  3. filtrationfiltered

Sources & evidence

ORD record
ord-0e85afbb4c4b4fdf8d26dc6496a80b66
Source dataset
uspto-grants-2007_03
Patent number
US07196111B2

Linked notes

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