4-Chlorobutyryl chloride → N-(1-bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazin-6-yl)-4-chloro-butyramide

HRID 1783730Notes

Reaction equation

HRID 1783730 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Br:16])=[N:7][N:8]([CH:13]([CH3:15])[CH3:14])[C:9]2=[O:12])=[CH:4][CH:3]=1.[Cl:17][CH2:18][CH2:19][CH2:20][C:21](Cl)=[O:22]>CN(C=O)C>[Br:16][C:6]1[C:5]2[C:10](=[CH:11][C:2]([NH:1][C:21](=[O:22])[CH2:20][CH2:19][CH2:18][Cl:17])=[CH:3][CH:4]=2)[C:9](=[O:12])[N:8]([CH:13]([CH3:14])[CH3:15])[N:7]=1

Participants

4

Reactant 2

HCID 783704-Chlorobutyryl chlorideHCID 211065807-Amino-2-Isopropyl-4-bromo-2H-phthalazin-1-one

Product 1

HCID 68980205N-(1-bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazin-6-yl)-4-chloro-butyramideYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-amino-2-isopropyl-4-bromo-2H-phthalazin-1-one (0.5 g, 1.8 mmol) in DMF (8 ml), was added TEA (0.28 ml, 1.98 mmol). After 5 min, 4-chlorobutyryl chloride (0.22 ml, 2.0 mmol) was added and the solution was stirred at RT for 2 hours. After this time LC-MS indicated the complete consumption of starting material and the mixture was diluted with DCM (30 ml) and washed with HCl (1M, 20 ml). The organic layer was separated, dried (MgSO4) and concentrated under vacuum. The residue was subjected to flash column chromatography (elution: 60% heptane, 40% EtOAc) to give N-(1-bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazin-6-yl)-4-chloro-butyramide (0.46 g, 67% yield) as a white solid.

Workup

  1. customthe complete consumption of starting material
  2. additionthe mixture was diluted with DCM (30 ml)
  3. washwashed with HCl (1M, 20 ml)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under vacuum
  7. washThe residue was subjected to flash column chromatography (elution: 60% heptane, 40% EtOAc)

Sources & evidence

ORD record
ord-932f3e1266274b2f9fedfcdfd892c19b
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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