2-(3,5-Dimethyladamantan-1-yl)acetic acid → 2-[3,5-dimethyl-1-adamantyl]-N-(4-isopropyl-1-oxophthalazin-2(1H)-yl)acetamide

HRID 469547Notes

Reaction equation

HRID 469547 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:15].[CH3:16][C:17]12[CH2:27][CH:21]3[CH2:22][C:23]([CH3:26])([CH2:25][C:19]([CH2:28][C:29](O)=[O:30])([CH2:20]3)[CH2:18]1)[CH2:24]2>>[CH3:26][C:23]12[CH2:22][CH:21]3[CH2:27][C:17]([CH3:16])([CH2:18][C:19]([CH2:28][C:29]([NH:1][N:2]4[N:11]=[C:10]([CH:12]([CH3:13])[CH3:14])[C:9]5[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=5)[C:3]4=[O:15])=[O:30])([CH2:20]3)[CH2:25]1)[CH2:24]2

Participants

3

Reactant 2

HCID 40675892-(3,5-Dimethyladamantan-1-yl)acetic acidHCID 671616462-amino-4-isopropylphthalazin-1(2H)-one

Product 1

HCID 532379652-[3,5-dimethyl-1-adamantyl]-N-(4-isopropyl-1-oxophthalazin-2(1H)-yl)acetamide

Procedure

The product from Example 1B and 2-(3,5-dimethyl-1-adamantyl)acetic acid were processed using the method described in Example 17C to afford the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 0.81 (s, 6H) 0.98-1.20 (m, 2H) 1.20-1.42 (m, 14H) 1.52 (s, 2H) 1.98-2.14 (m, 3H) 3.49-3.73 (m, 1H) 7.89 (t, J=7.48 Hz, 1H) 7.95-8.04 (m, 1H) 8.11 (d, J=8.24 Hz, 1H) 8.34 (d, J=6.71 Hz, 1H) 11.12 (s, 1H); MS (ESI) m/z 408 (M+H)+.

Sources & evidence

ORD record
ord-959adbca2a5c4868b911760aa7df0ec7
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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