Methylamine → HCID 21106540, compound

HRID 1765371Notes

Reaction equation

HRID 1765371 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)[N:3]=1.[C:22](N1C=CN=C1)([N:24]1C=CN=C1)=O.CN>CN(C=O)C.C1COCC1>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH:24][CH3:22])=[O:18])=[CH:15][CH:14]=2)[N:3]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 21106539HCID 21106539, compound

Product 1

HCID 21106540HCID 21106540, compoundYield 77.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Bromo-1-oxo-1H-phthalazin-2-yl)benzoic acid (0.15 g, 0.43 mmol) and 1,1′-carbonyldiimidazol (0.10 g, 0.65 mmol) were dissolved in DMF (10 ml) at room temperature. Methyl amine (0.33 ml of a 2M solution in THF, 0.65 mmol) were added and stirring was continued for 4 h. Evaporation of the solvent under reduced pressure, dilution with dichloromethane, extraction with a saturated aqueous NaHCO3 solution and evaporation of the solvent in vacuum gave the title compound (0.12 g, 77% yield) 1H-NMR: (400 MHz, D6-DMSO) 8.55 (1H, d), 8.38 (1H, d), 8.10 (1H, t), 8.03 (2H, d), 8.02 (2H, d), 7.73 (2H, d), 2.82 (3H, d).

Workup

  1. customEvaporation of the solvent under reduced pressure, dilution
  2. extractionwith dichloromethane, extraction
  3. customwith a saturated aqueous NaHCO3 solution and evaporation of the solvent in vacuum

Sources & evidence

ORD record
ord-158e7b1baebb4edda02387b7f0dc6b44
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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