Dimethylformamide dimethyl acetal → HCID 24771702, compound

HRID 1670702Notes

Reaction equation

HRID 1670702 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[NH2:9][C:10]1[CH:11]=[CH:12][C:13]2[N:33]([CH:34]=1)[C:16]1[N:17]([C:26]3[CH:27]=[N:28][C:29]([Cl:32])=[CH:30][CH:31]=3)[C:18](=[O:25])[C:19]3[C:24]([C:15]=1[N:14]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3>CN(C=O)C>[Cl:32][C:29]1[N:28]=[CH:27][C:26]([N:17]2[C:16]3[N:33]4[CH:34]=[C:10]([N:9]=[CH:3][N:4]([CH3:6])[CH3:5])[CH:11]=[CH:12][C:13]4=[N:14][C:15]=3[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]2=[O:25])=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 24771431HCID 24771431, compound

Product 1

HCID 24771702HCID 24771702, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

N,N-Dimethylformamide dimethyl acetal (10.0 equiv., 1.935 mmol, 0.231 g) was added to a suspension of compound 53 (1.0 equiv., 0.193 mmol, 0.070 g) in DMF (3 ml). The reaction mixture was stirred overnight at 110° C. The solvent was evaporated under reduced pressure. Isopropyl ether was added and the mixture was brought on a filter and washed with isopropyl ether to give 6-(6-chloro-pyridin-3-yl)-9-[[(dimethylamino)-methylene]amino]-pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one (84) (0.050 g, yield=62%, purity (LC)=77%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionIsopropyl ether was added
  3. filtrationa filter
  4. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-1f6f01a2d28f4e1eaadd543d10573347
Source dataset
uspto-grants-2011_08
Patent number
US07994187B2

Reaction notes

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