Formaldehyde → 8-{3-[(2-cyano-ethyl)-methyl-amino]-prop-1-ynyl}-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

HRID 1970052Notes

Reaction equation

C=O.[CH3:3][N:4]([CH2:9][C:10]#[CH:11])[CH2:5][CH2:6][C:7]#[N:8].C([C:14]1[CH:23]=[CH:22][C:21]2[NH:20][C:19](=[O:24])[C:18]3[NH:25][CH:26]=[CH:27][C:17]=3[C:16]=2[CH:15]=1)#C.[CH2:28]([C:30]([O-:32])=[O:31])[CH3:29]>O1CCOCC1.[Cu](I)I>[C:7]([CH2:6][CH2:5][N:4]([CH3:3])[CH2:9][C:10]#[C:11][C:14]1[CH:23]=[CH:22][C:21]2[NH:20][C:19](=[O:24])[C:18]3[NH:25][CH:26]=[CH:27][C:17]=3[C:16]=2[CH:15]=1)#[N:8].[CH2:28]([C:30]([O-:32])=[O:31])[CH3:29]

Participants

Conditions

Temperature: 110 °C

Procedure

31 mg (0.35 mmol) of para-formaldehyde, 35 mg (0.42 mmol) of 3-(methyl-prop-2-ynyl-amino)-propionitrile and 7 mg (0.04 mmol) of copper iodide are added to a suspension of 98 mg (0.35 mmol) of 8-ethynyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in 3 ml of anhydrous dioxan, then the mixture is heated at 110° C. for 6 hours. The raw reaction product is then filtered, and the filtrate is evaporated. The residue is triturated with methanol, then the new filtrate is evaporated. The product is recrystallized from methanol to give 10 mg (8%) of 8-{3-[(2-cyano-ethyl)-methyl-amino]-prop-1-ynyl}-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Workup

customThe raw reaction product
filtrationis then filtered
customthe filtrate is evaporated
customThe residue is triturated with methanol
customthe new filtrate is evaporated
customThe product is recrystallized from methanol

Sources & evidence

ORD record: ord-8796feb1ce2d4f999ecb6977cd85b6be
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426437B2

Reaction notes

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