1-Adamantaneacetic acid → 2-(adamantan-1-yl)-N-[4-(4-methylphenyl)-1-oxophthalazin-2(1H)-yl]acetamide

HRID 469633Notes

Reaction equation

HRID 469633 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:19].[C:20]12([CH2:30][C:31](O)=[O:32])[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH2:21]1)[CH2:27]2>>[C:20]12([CH2:30][C:31]([NH:1][N:2]3[N:11]=[C:10]([C:12]4[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=4)[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[C:3]3=[O:19])=[O:32])[CH2:27][CH:26]3[CH2:25][CH:24]([CH2:23][CH:22]([CH2:28]3)[CH2:21]1)[CH2:29]2

Participants

3

Reactant 2

HCID 1232211-Adamantaneacetic acidHCID 671623252-amino-4-(4-methylphenyl)-phthalazin-1(2H)-one

Product 1

HCID 532366252-(adamantan-1-yl)-N-[4-(4-methylphenyl)-1-oxophthalazin-2(1H)-yl]acetamide

Procedure

The product of Example 135A and 2-(adamantan-1-yl)acetic acid were treated using a method similar to that described in Example 17C to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.24 (s, 1H), 8.39-8.42 (m, 1H), 7.88-8.02 (m, 2H), 7.73-7.76 (m, 1H), 7.47-7.50 (m, 2H), 7.37-7.40 (m, 2H), 2.42 (s, 3H), 2.05 (s, 2H), 1.94-1.99 (m, 3H), 1.65-1.73 (m, 9H), 1.57-1.64 (m, 3H); MS (APCI+) M/Z 428 (M+H)+.

Sources & evidence

ORD record
ord-0db03a1689274cac901bcd09fa179870
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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