4-Chlorophenylacetyl chloride → 2-(4-chlorophenyl)-N-[1-oxo-4-(trifluoromethyl)phthalazin-2(1H)-yl]acetamide

HRID 469532Notes

Reaction equation

HRID 469532 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:16].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25](Cl)=[O:26])=[CH:20][CH:19]=1>>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([NH:1][N:2]2[N:11]=[C:10]([C:12]([F:15])([F:13])[F:14])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]2=[O:16])=[O:26])=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 906924-Chlorophenylacetyl chlorideHCID 671611112-amino-4-(trifluoromethyl)phthalazin-1(2H)-one

Product 1

HCID 532370662-(4-chlorophenyl)-N-[1-oxo-4-(trifluoromethyl)phthalazin-2(1H)-yl]acetamideYield 83.8%

Procedure

The product of Example 11B (41 mg) and 2-(4-chlorophenyl)acetyl chloride (0.030 mL, 0.20 mmol) were treated using a method similar to that described in Example 1C to give the title compound (57 mg, 0.15 mmol) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 11.90 (s, 1H), 8.42 (dd, 1H), 8.19-7.97 (m, 3H), 7.41 (dd, J=3.3 Hz, 4H), 3.74 (s, 2H); MS (DCI) M/Z 399.2 (M+NH4)+.

Sources & evidence

ORD record
ord-b9d8c8eda75f47c4a8cce4820e5b503a
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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