Dimethylformamide → HCID 178518378, compound

HRID 2236836Notes

Reaction equation

HRID 2236836 reaction equation
CO/[CH:3]=[C:4]1/[C:5](=[O:20])[NH:6][C:7](=[O:19])[C:8]2[C:13]/1=[CH:12][C:11]([N:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1)=[CH:10][CH:9]=2.CN(C)C=O.[Br:26][C:27]1[CH:28]=[CH:29][C:30]([NH2:33])=[N:31][CH:32]=1>CCOCC>[Br:26][C:27]1[CH:28]=[CH:29][C:30]([NH:33]/[CH:3]=[C:4]2\[C:5](=[O:20])[NH:6][C:7](=[O:19])[C:8]3[C:13]\2=[CH:12][C:11]([N:14]2[CH:15]=[CH:16][CH:17]=[CH:18]2)=[CH:10][CH:9]=3)=[N:31][CH:32]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 706222-Amino-5-bromopyridineHCID 59299993(E)-4-(methoxymethylene)-6-(1H-pyrrol-1-yl)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178518378HCID 178518378, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of (E)-4-(methoxymethylene)-6-(1H-pyrrol-1-yl)isoquinoline-1,3(2H,4H)-dione (268 mg, 1.0 mmole), dimethylformamide (8 mL), and 5-bromopyridin-2-amine (173 mg, 1.0 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 salmon solid, 176 mg, (43%), mp 317-8° C. dec; MS (ES−): m/z 407.0 (M−H).

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered
  3. washwashed with fresh ether
  4. customdried
  5. customto give a salmon solid, 176 mg, (43%), mp 317-8° C. dec

Sources & evidence

ORD record
ord-b85eb5e8ec8741bc9942fc68b3a1f76e
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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