1-Methylpiperazine → Desmethyl Carbodenafil

HRID 327050Notes

Reaction equation

HRID 327050 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][C:5]=1[C:13]1[NH:14][CH2:15][C:16]2[N:21]([CH3:22])[N:20]=[C:19]([CH2:23][CH2:24][CH3:25])[C:17]=2[N:18]=1)[CH3:2].[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.Cl.CN(C)CCCN=C=NCC.[OH:45]N1C2C=CC=CC=2N=N1>ClCCl>[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([N:30]2[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]2)=[O:10])=[CH:6][C:5]=1[C:13]1[NH:14][C:15](=[O:45])[C:16]2[N:21]([CH3:22])[N:20]=[C:19]([CH2:23][CH2:24][CH3:25])[C:17]=2[N:18]=1)[CH3:2]

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178440321HCID 178440321, compound

Product 1

HCID 135430839Desmethyl CarbodenafilYield 25.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-ethoxy-3-(1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-5-yl)benzoic acid (0.095 g, 0.00027 mol), 1-methylpiperazine (0.265 g, 0.00265 mol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.77 g, 0.0004 mol) and 1-hydroxybenzotriazole (0.054 g, 0.0004 mol) in dichloromethane (25 ) was stirred at room temperature for 18 hours. The reaction solution was washed with water (25 ml), dried (MgSO4) and evaporated under vacuum, and then the resulting residue crystallised from ethyl acetate-hexane to give the title compound as colourless crystals (0.03 g, 25%), m.p. 196°-197° C. Found C,63.12; H,6.81; N,18.96. C23H30N6O3 requires C,62.99; H,6.90; N,19.16%.

Workup

  1. washThe reaction solution was washed with water (25 ml)
  2. dry with materialdried (MgSO4)
  3. customevaporated under vacuum
  4. customthe resulting residue crystallised from ethyl acetate-hexane

Sources & evidence

ORD record
ord-79bb8673f33e4648988e5760ca6c7187
Source dataset
uspto-grants-1993_12
Patent number
US05272147

Reaction notes

Loading…