Dimethylformamide → HCID 178480146, compound

HRID 2236852Notes

Reaction equation

HRID 2236852 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]/OC.CN(C)C=O.[CH3:22][N:23]1[CH2:27][CH2:26][CH2:25][CH:24]1[C:28]1[CH:29]=[CH:30][C:31]([NH2:34])=[N:32][CH:33]=1>CCOCC>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:34][C:31]1[CH:30]=[CH:29][C:28]([CH:24]2[CH2:25][CH2:26][CH2:27][N:23]2[CH3:22])=[CH:33][N:32]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31107895-(1-Methylpyrrolidin-2-yl)pyridin-2-amineHCID 68691018(E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178480146HCID 178480146, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of (E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (696 mg, 2.12 mmole), dimethylformamide (15 mL), and 5-(1-methylpyrrolidin-2-yl)pyridin-2-amine (375 mg, 2.12 mmole) is heated at 125° C. for four hours. The reaction mixture is cooled, diluted with ether, filtered, washed with fresh ether and dried to give a yellow solid, 580 mg, (58%), mp 174-206° C. dec; MS (ES+): m/z 475.0 (M+H).

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered
  3. washwashed with fresh ether
  4. customdried
  5. customto give a yellow solid, 580 mg, (58%), mp 174-206° C. dec

Sources & evidence

ORD record
ord-d3bcbbc2082d406a8ded1dfe520e1a24
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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