4-Amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide → Sildenafil

HRID 1507681Notes

Reaction equation

HRID 1507681 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([NH2:9])=[O:8])=[C:5]([NH2:10])[C:4]([CH2:11][CH2:12][CH3:13])=[N:3]1.[CH2:14]([O:16][C:17]1[CH:25]=[CH:24][C:23]([S:26]([N:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)(=[O:28])=[O:27])=[CH:22][C:18]=1[C:19](Cl)=O)[CH3:15]>>[CH3:13][CH2:12][CH2:11][C:4]1[C:5]2[N:10]=[C:19]([C:18]3[CH:22]=[C:23]([S:26]([N:29]4[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH2:34]4)(=[O:27])=[O:28])[CH:24]=[CH:25][C:17]=3[O:16][CH2:14][CH3:15])[NH:9][C:7](=[O:8])[C:6]=2[N:2]([CH3:1])[N:3]=1

Participants

3

Reactant 2

HCID 33380444-Amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamideHCID 54158580HCID 54158580, compound

Product 1

HCID 135398744Sildenafil

Procedure

An reaction between 1-methyl-3-propyl-4-aminopyrazole-5-carboxamide and 2-ethoxy-5-(4-methylpiperazine-1-sulfonyl)-benzoyl chloride is performed, and then Sildenafil is obtained by ring closure.

Sources & evidence

ORD record
ord-0efa5b7169a44c14b785c9ab6f74c71b
Source dataset
uspto-grants-2015_12
Patent number
US09221825B2

Reaction notes

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