Triethylamine → HCID 57860716, compound

HRID 1947165Notes

Reaction equation

HRID 1947165 reaction equation
[CH3:1][O:2][C:3]1[C:7]2[C:8](=[O:16])[NH:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[N:5]([CH3:17])[C:4]=1[C:18]([NH:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)=[O:19].C(N(CC)CC)C.[C:34]([O:37][CH2:38][C:39](Cl)=[O:40])(=[O:36])[CH3:35]>C1COCC1.C(=O)([O-])O.[Na+]>[C:34]([O:37][CH2:38][C:39]([N:24]1[CH2:25][CH2:26][CH:21]([NH:20][C:18]([C:4]2[N:5]([CH3:17])[C:6]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[NH:9][C:8](=[O:16])[C:7]=3[C:3]=2[O:2][CH3:1])=[O:19])[CH2:22][CH2:23]1)=[O:40])(=[O:36])[CH3:35]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 66893409HCID 66893409, compound

Product 1

HCID 57860716HCID 57860716, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-methoxy-1-methyl-4-oxo-N-piperidin-4-yl-4,5-dihydro-1H-pyrrolo[3,2-c]quinoline-2-carboxamide (300 mg, 0.87 mmol) and triethylamine (88 mg, 0.87 mmol) in THF (30 mL) was added acetoxyacetyl chloride (119 mg, 0.87 mmol) under ice-cooling, and the mixture was stirred for 2 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated. The obtained solid was washed with diethyl ether-hexane to give the title compound (221 mg, 56%) as a white solid.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated
  5. washThe obtained solid was washed with diethyl ether-hexane

Sources & evidence

ORD record
ord-b35e51715cb443198b18046f8fea60fd
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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