Acetic Acid → 5-{5-[[(Acetyloxy)imino](amino)methyl]-2-isobutoxy-3-pyridinyl}-2-methyl-3-propyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 354186Notes

Reaction equation

HRID 354186 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([O:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[C:9]([C:11]2[NH:12][C:13](=[O:24])[C:14]3[C:15](=[C:17]([CH2:21][CH2:22][CH3:23])[N:18]([CH3:20])[N:19]=3)[N:16]=2)[CH:10]=1)=[NH:4].[C:30](O)(=[O:32])[CH3:31].Cl.CN(C)CCCN=C=NCC>O1CCOCC1>[C:30]([O:1][N:2]=[C:3]([NH2:4])[C:5]1[CH:10]=[C:9]([C:11]2[NH:12][C:13](=[O:24])[C:14]3[C:15](=[C:17]([CH2:21][CH2:22][CH3:23])[N:18]([CH3:20])[N:19]=3)[N:16]=2)[C:8]([O:25][CH2:26][CH:27]([CH3:28])[CH3:29])=[N:7][CH:6]=1)(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178438342HCID 178438342, compound

Product 1

HCID 1363883775-{5-[[(Acetyloxy)imino](amino)methyl]-2-isobutoxy-3-pyridinyl}-2-methyl-3-propyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-oneYield 82.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-Hydroxy-6-isobutoxy-5-(2-methyl-7-oxo-3-propyl-6,7-dihydro-2H-pyrazolo[4,3-d]pyrimidin-5-yl)-3-pyridinecarboximidamide (Example 39) (65 mg, 0.16 mmol), N,N-dimethylaminopyridine (24 mg, 0.20 mmol), acetic acid (9.7 mg, 0.16 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (37.5 mg, 0.20 mmol) were stirred in dioxan (2 mL) for 14 h. The solvent was removed in vacuo and the product purified by flash column chromatography (eluting with 90% dichloromethane:methanol) to give the product (58 mg) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe product purified by flash column chromatography (eluting with 90% dichloromethane:methanol)

Sources & evidence

ORD record
ord-55cd0daca4644c1eabd30e8b1ef305d7
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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