Ethyl orthoformate → HCID 178480743, compound

HRID 2236596Notes

Reaction equation

HRID 2236596 reaction equation
Br[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:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)=[CH:18][CH:17]=1.[N+:29](C1C=C2C(=CC=1)C(=O)NC(=O)C2)([O-:31])=[O:30].CN1CCN(CC2C=CC(N)=CC=2)CC1.C(OCC)(OCC)OCC>C(O)CO>[N+:29]([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:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)=[CH:18][CH:17]=1)([O-:31])=[O:30]

Participants

6

Reactant 4

HCID 31214Ethyl orthoformateHCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 592999676-nitroisoquinoline-1,3(2H,4H)-dioneHCID 178480719HCID 178480719, compound

Product 1

HCID 178480743HCID 178480743, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Using the procedure described for (4Z)-6-bromo-4-({[4-(4-methylpiperazin-1-yl)phenyl}amino}methylene)isoquinoline-1,3(2H,4H)-dione (Example 27), 0.21 g (1.0 mmol) of 6-nitroisoquinoline-1,3(2H,4H)-dione, 0.20 g of 4-(4-methylpiperazin-1-yl)methyl-phenylamine, 0.18 ml (1.1 mmol) of triethyl orthoformate, and 2.0 ml of ethylene glycol were reacted to give 0.13 g (32%) of amber solid, mp 250-2600 (dec); MS (ES+) m/z 408.2 (M+H)+1

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-8193accd892046e8bbbaaf20bc18ae7a
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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