Acetic Acid → HCID 86627511, compound

HRID 1969985Notes

Reaction equation

HRID 1969985 reaction equation
C=O.[C:3](O)(=O)C.[C:7]([BH3-])#[N:8].[Na+].N[C:12]1[CH:21]=[CH:20][C:19]2[NH:18][C:17](=[O:22])[C:16]3[NH:23][CH:24]=[CH:25][C:15]=3[C:14]=2[CH:13]=1.[CH2:26]([C:28]([O-:30])=[O:29])[CH3:27]>C(O)C>[CH3:3][N:8]([CH3:7])[C:12]1[CH:21]=[CH:20][C:19]2[NH:18][C:17](=[O:22])[C:16]3[NH:23][CH:24]=[CH:25][C:15]=3[C:14]=2[CH:13]=1.[CH2:26]([C:28]([O-:30])=[O:29])[CH3:27]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 712Formaldehyde2×HCID 5003444Sodium cyanoborohydride2×HCID 86627489HCID 86627489, compound

Product 1

HCID 86627511HCID 86627511, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

33 μL (0.41 mmol) of a 37% aqueous solution of formaldehyde, 20 μL (0.35 mmol) of acetic acid and 26 mg (0.41 mmol) of sodium cyanoborohydride are added to 100 mg (0.37 mmol) of 8-amino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate (synthesis 64) suspended in 1.2 ml of ethanol. The mixture is stirred for 6 hours at room temperature then 33 μL (0.41 mmol) of a 37% aqueous solution of formaldehyde, 20 μL (0.35 mmol) of acetic acid and 7 mg (0.11 mmol) of sodium cyanoborohydride are added again. The reaction mixture is stirred overnight at room temperature. The solvents are evaporated and the residue obtained is purified by preparative LCMS to give 5 mg (5%) of 8-dimethylamino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Workup

  1. stirringThe reaction mixture is stirred overnight at room temperature
  2. customThe solvents are evaporated
  3. customthe residue obtained
  4. customis purified by preparative LCMS

Sources & evidence

ORD record
ord-817136b1aa6c46aeb383b068b2665a36
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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