1-Adamantaneacetyl chloride → HCID 67160633, compound

HRID 469665Notes

Reaction equation

HRID 469665 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([Br:20])=[CH:7][CH:8]=2)[C:3]1=[O:21].[C:22]12([CH2:32][C:33](Cl)=[O:34])[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH2:23]1)[CH2:29]2>>[C:22]12([CH2:32][C:33]([NH:1][N:2]3[N:11]=[C:10]([C:12]4[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=4)[C:9]4[C:4](=[CH:5][C:6]([Br:20])=[CH:7][CH:8]=4)[C:3]3=[O:21])=[O:34])[CH2:29][CH:28]3[CH2:27][CH:26]([CH2:25][CH:24]([CH2:30]3)[CH2:23]1)[CH2:31]2

Participants

3

Reactant 2

HCID 27718821-Adamantaneacetyl chlorideHCID 67161115HCID 67161115, compound

Product 1

HCID 67160633HCID 67160633, compound

Procedure

The product from Example 174A and 2-(adamant-1-yl)acetyl chloride were treated using a method similar to that described in Example 53 to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 11.28 (s, 1H), 8.50 (d, J=2.1 Hz, 1H), 8.14 (dd, J=8.6, 2.2 Hz, 1H), 7.70 (d, J=8.7 Hz, 1H), 7.51-7.55 (m, 2H), 7.11-7.15 (m, 2H), 3.85 (s, 3H), 2.05 (s, 2H), 1.92-1.98 (bs, 3H), 1.58-1.70 (m, 12H); MS (ESI+) M/Z, 524 (M+H)+.

Sources & evidence

ORD record
ord-2f60201a508847318a8c7b1af6e74787
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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