Hydrochloric Acid → 4-(3-(N-(5-chloropentanoyl)amino)phenyl)-5,6,7,8-tetrahydrophthalazin-1(2H)-one

HRID 749103Notes

Reaction equation

HRID 749103 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[NH2:9][C:10]1[CH:11]=[C:12]([C:16]2[C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=3[C:19](=[O:26])[NH:18][N:17]=2)[CH:13]=[CH:14][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].Cl>O1CCCC1.O>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:9][C:10]1[CH:11]=[C:12]([C:16]2[C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=3[C:19](=[O:26])[NH:18][N:17]=2)[CH:13]=[CH:14][CH:15]=1)=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium Carbonate2×HCID 740895-Chlorovaleryl chloride2×HCID 230325814-(3-aminophenyl)-5,6,7,8-tetrahydrophthalazin-1(2H)-one

Product 1

HCID 669663514-(3-(N-(5-chloropentanoyl)amino)phenyl)-5,6,7,8-tetrahydrophthalazin-1(2H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

5-chloropentanoyl chloride (171 mg) was added dropwise to a mixed solution of the compound prepared in Example 1 (241 mg) and potassium carbonate (89.8 mg) in tetrahydrofuran (3.00 mL) and water (1.00 mL) in ice bath and the mixture was stirred for 30 minutes. Moreover, potassium carbonate (45.0 mg) and 5-chloropentanoyl chloride (85.5 mg) was added the reaction mixture, which was stirred for 30 minutes. 1N hydrochloric acid was added to the reaction mixture, which was adjusted to pH 2. Water was added thereto and the deposited crystal was collected by filtration. It was washed with water and hexane sequentially and dried under reduced pressure to give the compound of the present invention (347 mg) having the following physical data.

Workup

  1. stirringwas stirred for 30 minutes
  2. filtrationthe deposited crystal was collected by filtration
  3. washIt was washed with water and hexane sequentially
  4. customdried under reduced pressure
  5. customto give the compound of the present invention (347 mg)

Sources & evidence

ORD record
ord-6f715311f9a44c5f9a1ca337bf778988
Source dataset
uspto-grants-2008_07
Patent number
US07402580B2

Reaction notes

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