Triethylamine → HCID 178480452, compound

HRID 2236713Notes

Reaction equation

HRID 2236713 reaction equation
[Br: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.[CH3:17][N:18]([CH:26]1[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27]1)[C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1.C(N(CC)CC)C>CN(C)C=O>[Br: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:25][C:22]1[CH:21]=[CH:20][C:19]([N:18]([CH3:17])[CH:26]2[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27]2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dioneHCID 68693629HCID 68693629, compound

Product 1

HCID 178480452HCID 178480452, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4E)-6-Bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.17 g, 0.61 mmol) and N-methyl-N-(1-methyl-pyrrolidin-3-yl)-benzene-1,4-diamine (0.12 g, 0.61 mmol) were stirred in N,N-dimethylformamide (3 mL) and triethylamine (0.16 mL) at 60-70° C. The reaction mixture is quenched by the addition of water. The solid material is then collected, washed with diethyl ether, water, and methanol, and then dried under vacuum to give (4Z)-6-bromo-4-[({4-[methyl(1-methylpyrrolidin-3-yl)amino]phenyl}amino)methylene]isoquinoline-1,3(2H,4H)-dione (0.12 g, 44%) as a rust colored powder.

Workup

  1. customat 60-70° C
  2. customThe reaction mixture is quenched by the addition of water
  3. customThe solid material is then collected
  4. washwashed with diethyl ether, water, and methanol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-77145127eef64988b79c2f09d0d1ccdc
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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