Triethylamine → HCID 178480432, compound

HRID 2236696Notes

Reaction equation

HRID 2236696 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]1[CH2:24][CH2:23][CH2:22][N:21]([C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)[CH2:20][CH2:19]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:31][C:28]1[CH:27]=[CH:26][C:25]([N:21]2[CH2:22][CH2:23][CH2:24][N:18]([CH3:17])[CH2:19][CH2:20]2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 130079514-(4-Methyl-1,4-diazepan-1-yl)anilineHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178480432HCID 178480432, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.15 g, 0.54 mmol) and [4-(4-methyl-1,4-diazepan-1-yl)phenyl]amine (0.11 g, 0.54 mmol) were stirred in N,N-dimethylformamide (3 mL) with triethylamine (0.3 mL). The reaction mixture is quenched by the addition of water. The solid material is then collected, washed with diethyl ether, water, and methanol. The crude material is dissolved in a minimum of 5% methanol in chloroform and then passed through a Florisil plug, eluting with 5% methanol in chloroform. The filtrate is concentrated under reduced pressure to give and then dried under vacuum to give (4Z)-6-bromo-4-({[4-(4-methyl-1,4-diazepan-1-yl)phenyl]amino}methylene)isoquinoline-1,3(2H,4H)-dione (64 mg, 26%) as a rust colored powder.

Workup

  1. customThe reaction mixture is quenched by the addition of water
  2. customThe solid material is then collected
  3. washwashed with diethyl ether, water, and methanol
  4. dissolutionThe crude material is dissolved in a minimum of 5% methanol in chloroform
  5. washeluting with 5% methanol in chloroform
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. customto give
  8. customdried under vacuum

Sources & evidence

ORD record
ord-65a57583d12f452c937234a6c7a9eec3
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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