Dimethylformamide dimethyl acetal → ethyl 3-cyano-2-[(E)-dimethylaminomethylideneamino]-5,7-dihydro-4H-furo[2,3-c]pyridine-6-carboxylate

HRID 38533Notes

Reaction equation

HRID 38533 reaction equation
[NH2:1][C:2]1[O:15][C:5]2[CH2:6][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:16]#[N:17].CO[CH:20](OC)[N:21]([CH3:23])[CH3:22]>>[C:16]([C:3]1[C:4]2[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][C:5]=2[O:15][C:2]=1/[N:1]=[CH:20]/[N:21]([CH3:23])[CH3:22])#[N:17]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 58116828Ethyl 2-amino-3-cyano-4,7-dihydrofuro[2,3-c]pyridine-6(5H)-carboxylate

Product 1

HCID 58116902ethyl 3-cyano-2-[(E)-dimethylaminomethylideneamino]-5,7-dihydro-4H-furo[2,3-c]pyridine-6-carboxylateYield 98.2%

Procedure

Ethyl 2-amino-3-cyano-4,7-dihydrofuro[2,3-c]pyridine-6(5H)-carboxylate from Example 36A (7.00 g, 29.8 mmol) was heated in dimethylformamide dimethylacetal (14.7 mL, 110 mmol) for 30 min to 110° C. The mixture was then concentrated in vacuo, and the residue was triturated with petroleum ether, the solvent was decanted, and the trituration was repeated. The remaining solid was then triturated with diethyl ether/petroleum ether (1:1), and the precipitate was collected by suction filtration to yield 8.5 g (98%) of the title compound.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue was triturated with petroleum ether
  3. customthe solvent was decanted
  4. customThe remaining solid was then triturated with diethyl ether/petroleum ether (1:1)
  5. filtrationthe precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-cd6a9ede643640a1a846cbef67ddd10c
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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