Formic Acid → HCID 24771433, compound

HRID 1670699Notes

Reaction equation

HRID 1670699 reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[NH2:11][C:12]1[CH:13]=[CH:14][C:15]2[N:35]([CH:36]=1)[C:18]1[N:19]([C:28]3[CH:29]=[N:30][C:31]([Cl:34])=[CH:32][CH:33]=3)[C:20](=[O:27])[C:21]3[C:26]([C:17]=1[N:16]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3>ClCCl>[Cl:34][C:31]1[N:30]=[CH:29][C:28]([N:19]2[C:18]3[N:35]4[CH:36]=[C:12]([NH:11][CH:1]=[O:2])[CH:13]=[CH:14][C:15]4=[N:16][C:17]=3[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=[O:27])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 24771431HCID 24771431, compound

Product 1

HCID 24771433HCID 24771433, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Formic acid (5.0 equiv., 1.390 mmol, 0.064 g) was added to a cooled (0° C.) solution of acetic anhydride (2.0 equiv., 0.552 mmol, 0.050 g) in dichloromethane (1 ml). The reaction mixture was stirred at room temperature for 1 h. Compound 53 (1.0 equiv., 0.276 mmol, 0.100 g) was added and the resulting suspension was stirred at room temperature for 6 h. The precipitate was filtered off and successively washed with isopropanol and isopropyl ether affording N-[6-(6-chloro-pyridin-3-yl)-5,6-dihydro-5-oxo-pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-9-yl]-formamide (57) (0.060 g, yield=56%, purity (LC)=96%).

Workup

  1. stirringthe resulting suspension was stirred at room temperature for 6 h
  2. filtrationThe precipitate was filtered off
  3. washsuccessively washed with isopropanol and isopropyl ether

Sources & evidence

ORD record
ord-02fe4970a7e549ef834180f4479b340e
Source dataset
uspto-grants-2011_08
Patent number
US07994187B2

Reaction notes

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