3-(Trifluoromethoxy)phenylacetic Acid → N-[4-(4-chlorophenyl)-1-oxophthalazin-2(1H)-yl]-2-[3-(trifluoromethoxy)phenyl]acetamide

HRID 469599Notes

Reaction equation

HRID 469599 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:19].[F:20][C:21]([F:34])([F:33])[O:22][C:23]1[CH:24]=[C:25]([CH2:29][C:30](O)=[O:31])[CH:26]=[CH:27][CH:28]=1>>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3](=[O:19])[N:2]([NH:1][C:30](=[O:31])[CH2:29][C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([O:22][C:21]([F:33])([F:20])[F:34])[CH:24]=3)[N:11]=2)=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 27773163-(Trifluoromethoxy)phenylacetic AcidHCID 671613672-amino-4-(4-chlorophenyl)phthalazin-1(2H)-one

Product 1

HCID 53239110N-[4-(4-chlorophenyl)-1-oxophthalazin-2(1H)-yl]-2-[3-(trifluoromethoxy)phenyl]acetamide

Procedure

The product of Example 86A and 2-[3-(trifluoromethoxy)phenyl]acetic acid were treated using a method similar to that described in Example 57 to give the title compound. 1H NMR (500 MHz, DMSO-d6/Deuterium Oxide) δ ppm 8.41-8.43 (m, 1H), 7.95-8.02 (m, 2H), 7.73-7.75 (m, 1H), 7.63-7.64 (m, 4H), 7.50 (t, J=7.9 Hz, 1H), 7.42 (d, J=7.8 Hz, 1H), 7.38-7.40 (bs, 1H), 7.27-7.30 (m, 1H), 3.79 (s, 2H); MS (ESI−) M/Z 472 (M−H)−.

Sources & evidence

ORD record
ord-417c220d20904b639888f5e369a7ae30
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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