Dimethyl methoxymethylenemalonate → HCID 178498784, compound

HRID 510074Notes

Reaction equation

HRID 510074 reaction equation
Cl.[F:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8]([C:15](=[NH:17])[NH2:16])=[N:7]1.C[O:23][CH:24]=[C:25]([C:30](OC)=O)[C:26]([O:28][CH3:29])=[O:27].C[O-].[Na+]>CO>[F:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8]([C:15]2[N:16]=[C:24]([OH:23])[C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:30][N:17]=2)=[N:7]1

Participants

5

Reactant 3

HCID 90770Dimethyl methoxymethylenemalonateHCID 10942334Sodium MethoxideHCID 574158441-((2-Fluorophenyl)methyl)-1H-pyrazolo(3,4-b)pyridine-3-carboximidamide hydrochloride

Product 1

HCID 178498784HCID 178498784, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10.0 g (32.7 mmol) of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide hydrochloride (example 5A) and 8.54 g (49.1 mmol) of dimethyl (methoxymethylene)malonate were initially charged in 400 ml of methanol, and 1.77 g (32.7 mmol) of sodium methoxide were added cautiously. The mixture was reacted at 50° C. overnight. The precipitate formed was filtered off, washed with a little methanol and dried under high vacuum. Thus, 6.54 g (52% of theory) of the target compound were obtained.

Workup

  1. customThe mixture was reacted at 50° C. overnight
  2. customThe precipitate formed
  3. filtrationwas filtered off
  4. washwashed with a little methanol
  5. customdried under high vacuum
  6. customThus, 6.54 g (52% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-c7a0713403f8489bbeb892cf35e27670
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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