1-Adamantaneacetyl chloride → 2-(adamantan-1-yl)-N-[4-isopropyl-1-oxo-7-(trifluoromethyl)phthalazin-2(1H)-yl]acetamide

HRID 469663Notes

Reaction equation

HRID 469663 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[C:9]2[C:4](=[CH:5][C:6]([C:15]([F:18])([F:17])[F:16])=[CH:7][CH:8]=2)[C:3]1=[O:19].[C:20]12([CH2:30][C:31](Cl)=[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]([CH:12]([CH3:14])[CH3:13])[C:9]4[C:4](=[CH:5][C:6]([C:15]([F:18])([F:16])[F:17])=[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 27718821-Adamantaneacetyl chlorideHCID 67161250HCID 67161250, compound

Product 1

HCID 671615392-(adamantan-1-yl)-N-[4-isopropyl-1-oxo-7-(trifluoromethyl)phthalazin-2(1H)-yl]acetamide

Procedure

The product from Example 173A and 2-(adamantan-1-yl)acetyl chloride were treated as in Example 1C to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 11.19-11.28 (m, 1H), 8.58 (s, 1H), 8.28-8.40 (m, 2H), 3.58-3.70 (m, 1H), 2.04 (s, 2H), 1.93-1.98 (bs, 3H), 1.55-1.75 (m, 12H), 1.27 (d, J=6.7 Hz, 6H); MS (ESI+) M/Z 448 (M+H)+.

Sources & evidence

ORD record
ord-c7db735cca054d86a6582d1e31a94a93
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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