1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 135874413, compound

HRID 499253Notes

Reaction equation

HRID 499253 reaction equation
[CH2:1]([N:4]1[C:11]([NH2:12])=[C:10]([NH2:13])[C:8](=[O:9])[N:7]([CH2:14][CH2:15][CH3:16])[C:5]1=[O:6])[CH2:2][CH3:3].[CH3:17][C:18]1[N:22]([CH2:23][C:24](=[O:32])[NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:21]=[C:20]([C:33](O)=O)[CH:19]=1.CCN=C=NCCCN(C)C.Cl>CO>[O:6]=[C:5]1[N:4]([CH2:1][CH2:2][CH3:3])[C:11]2[N:12]=[C:33]([C:20]3[CH:19]=[C:18]([CH3:17])[N:22]([CH2:23][C:24]([NH:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:32])[N:21]=3)[NH:13][C:10]=2[C:8](=[O:9])[N:7]1[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedioneHCID 68416508HCID 68416508, compound

Product 1

HCID 135874413HCID 135874413, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,3-dipropyl-5,6-diaminouracil (2.20 mmol), in MeOH (10 mL), is added an equimolar amount of the title C compound, 5-methyl-1-phenylcarbamoylmethyl-1H-pyrazole-3-carboxylic acid, and EDCl (2.21 mmol). The reaction mixture is stirred at RT for 4-5 h while being monitored by TLC. The solvent is concentrated in vacuo and the amide intermediate is precipitated by the addition of water. After filtration, the solid is dissolved in MeOH (10 mL) and aqueous NaOH (2.5 N, 15 mL) and the mixture is stirred at 50-60° C. for 1 h. The MeOH is distilled off, and the residue is taken up in H2O and acidified with HCl to pH 4-5. The precipitate is collected by filtration, washed with water, and purified by flash chromatography (ethyl acetate-petroleum ether) to afford 2-[3-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-5-methyl-pyrazol-1-yl]-N-phenyl-acetamide: m.p. 255-257° C.; 1H-NMR (DMSO-d6) δ 0.87 (m, 6H), 1.56 (q, 2H), 1.70 (q, 2H), 2.32 (s, 3H), 3.84 (m, 2H), 3.98 (m, 2H), δ0.08 (s, 2H), 6.74 (s, 1H), 7.08 (m, 1H), 7.33 (m, 2H), 7.59 (m, 2H), 10.41 (s, 1H), 13.85 (s, 1H).

Workup

  1. concentrationThe solvent is concentrated in vacuo
  2. customthe amide intermediate is precipitated by the addition of water
  3. filtrationAfter filtration
  4. dissolutionthe solid is dissolved in MeOH (10 mL)
  5. stirringaqueous NaOH (2.5 N, 15 mL) and the mixture is stirred at 50-60° C. for 1 h
  6. distillationThe MeOH is distilled off
  7. filtrationThe precipitate is collected by filtration
  8. washwashed with water
  9. custompurified by flash chromatography (ethyl acetate-petroleum ether)

Sources & evidence

ORD record
ord-7baa921348f84d15990174af54be09eb
Source dataset
uspto-grants-2010_08
Patent number
US07767685B2

Reaction notes

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