Acetic Acid → 6-(2,4-Dichlorophenyl)-2-[(4-methylpiperazin-1-yl)methyl]pyrazolo[1,5-a]pyrazin-4(5H)-one

HRID 57678Notes

Reaction equation

HRID 57678 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:10][C:11](=[O:20])[C:12]2[N:13]([N:15]=[C:16]([CH:18]=O)[CH:17]=2)[CH:14]=1.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(O)(=O)C.C([BH3-])#N.[Na+].Cl>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:10][C:11](=[O:20])[C:12]2[N:13]([N:15]=[C:16]([CH2:18][N:25]3[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]3)[CH:17]=2)[CH:14]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 531671-MethylpiperazineHCID 5003444Sodium cyanoborohydrideHCID 58170006HCID 58170006, compound

Product 1

HCID 581700886-(2,4-Dichlorophenyl)-2-[(4-methylpiperazin-1-yl)methyl]pyrazolo[1,5-a]pyrazin-4(5H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

145 mg (0.32 mmol) of 6-(2,4-dichlorophenyl)-4-oxo-4,5-dihydropyrazolo[1,5-a]pyrazine-2-carbaldehyde (Example 18A) were dissolved in 6 ml of methanol, and 64 mg (0.64 mmol) of 1-methylpiperazine, 4 Å molecular sieve and 58 mg (0.96 mmol) of acetic acid were added. Finally, 40.2 mg (0.64 mmol) of sodium cyanoborohydride were added and the mixture was stirred at RT for 15 h. The crude mixture was acidified with 2N hydrochloric acid and the resulting precipitate was filtered off with suction. This gave 120 mg (96% of theory) of the product as a solid which was reacted further without any further purification.

Workup

  1. filtrationthe resulting precipitate was filtered off with suction
  2. customThis gave 120 mg (96% of theory) of the product as a solid which was reacted further without any further purification

Sources & evidence

ORD record
ord-1e6299af066c46c38fa367d1a99262dd
Source dataset
uspto-grants-2016_09
Patent number
US09434731B2

Reaction notes

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