2-(3-Hydroxyadamantan-1-yl)acetic acid → 2-(3-hydroxyadamantan-1-yl)-N-(4-isopropyl-1-oxophthalazin-2(1H)-yl)acetamide

HRID 469575Notes

Reaction equation

HRID 469575 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].[OH:16][C:17]12[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][C:19]([CH2:27][C:28](O)=[O:29])([CH2:20]3)[CH2:18]1)[CH2:24]2>>[OH:16][C:17]12[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][C:19]([CH2:27][C:28]([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:29])([CH2:20]3)[CH2:18]1)[CH2:24]2

Participants

3

Reactant 2

HCID 4293072-(3-Hydroxyadamantan-1-yl)acetic acidHCID 671616462-amino-4-isopropylphthalazin-1(2H)-one

Product 1

HCID 671600602-(3-hydroxyadamantan-1-yl)-N-(4-isopropyl-1-oxophthalazin-2(1H)-yl)acetamide

Procedure

The product of Example 1B and 2-(3-hydroxyadamantan-1-yl)acetic acid were processed using a method similar to that described in Example 17C to afford the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 11.12 (s, 1H), 8.34 (dd, J=7.9, 1.3 Hz, 1H), 8.11 (d, J=8.1 Hz, 1H), 8.00 (ddd, J=8.3, 7.1, 1.3 Hz, 1H), 7.89 (ddd, J=8.0, 7.1, 1.0 Hz, 1H), 3.61 (p, J=6.7 Hz, 1H), 2.08-2.11 (m, 4H), 1.36-1.63 (m, 13H), 1.26 (d, J=6.7 Hz, 6H); MS (ESI) m/z 396 (M+H)+.

Sources & evidence

ORD record
ord-c97e7ec9999b4051ab865b179a5cae1e
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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