Dimethylformamide → HCID 178507569, compound

HRID 2236602Notes

Reaction equation

HRID 2236602 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.CN1CCN([C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)CC1.[CH3:31][N:32](C)C=O>>[NH2:30][C:27]1[CH:28]=[C:29]([CH:24]=[CH:25][CH:26]=1)[CH2:31][NH:32]/[CH:14]=[C:5]1\[C:6](=[O:13])[NH:7][C:8](=[O:12])[C:9]2[C:4]\1=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 686927644-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dione

Product 1

HCID 178507569HCID 178507569, compoundYield 33%

Procedure

A mixture of 6-bromo-4-methoxymethylene-4H-isoquinoline-1,3-dione (141 mg, 0.5 mmol), 4-(4-methyl-piperazin-1-yl)-phenylamine (61.1 mg, 0.5 mmol) in 1 mL of N,N-dimethylformamide is stirred at room temperature for 40 min. After cooling in the refrigerator, the precipitate is collected, and washed with ether to give 61 mg (33%) of yellow solid mp 214-215° C.; HRMS (ESI) m/z calcd for C17H14BrN3O2 370.01966. found 370.01900 (M+H)−1, Analysis for C17H14BrN3O2 (0.33H2O); Calcd: C, 53.98; H, 3.91; N, 11.11. Found: C, 54.07; H, 3.52; N, 10.91.

Workup

  1. temperatureAfter cooling in the refrigerator
  2. customthe precipitate is collected
  3. washwashed with ether

Sources & evidence

ORD record
ord-554dfdc43a9c4b5197308e3ead0f52d6
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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