Acetic Acid → 8-(3-morpholin-4-yl-prop-1-ynyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

HRID 1970051Notes

Reaction equation

HRID 1970051 reaction equation
C=O.[NH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[C:9]([C:11]1[CH:20]=[CH:19][C:18]2[NH:17][C:16](=[O:21])[C:15]3[NH:22][CH:23]=[CH:24][C:14]=3[C:13]=2[CH:12]=1)#[CH:10].[CH2:25]([C:27]([O-:29])=[O:28])[CH3:26].C(O)(=O)C>O1CCOCC1.[Cu](I)I>[N:3]1([CH2:25][C:10]#[C:9][C:11]2[CH:20]=[CH:19][C:18]3[NH:17][C:16](=[O:21])[C:15]4[NH:22][CH:23]=[CH:24][C:14]=4[C:13]=3[CH:12]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[CH2:25]([C:27]([O-:29])=[O:28])[CH3:26]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 8083MorpholineHCID 866275508-ethynyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

Product 1

HCID 866275578-(3-morpholin-4-yl-prop-1-ynyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylateYield 12.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

15 mg (0.17 mmol) of para-formaldehyde, 15 mg (0.17 mmol) of morpholine and 3 mg (0.02 mmol) of copper iodide are added to a suspension of 47 mg (0.17 mmol) of 8-ethynyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in 5 ml of anhydrous dioxan, then a drop of acetic acid is added and the mixture is heated at 85° C. for 48 hours. The raw reaction product is then filtered, the filtrate is evaporated and the residue is purified by preparative LCMS to give 4 mg (6%) of 8-(3-morpholin-4-yl-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

  1. customThe raw reaction product
  2. filtrationis then filtered
  3. customthe filtrate is evaporated
  4. customthe residue is purified by preparative LCMS

Sources & evidence

ORD record
ord-8238585474ac455e8dddcc24e92d73f8
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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