1-Adamantaneacetyl chloride → HCID 53236389, compound

HRID 469651Notes

Reaction equation

HRID 469651 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:20].[C:21]12([CH2:31][C:32](Cl)=[O:33])[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH2:22]1)[CH2:28]2>>[C:21]12([CH2:31][C:32]([NH:1][N:2]3[N:11]=[C:10]([C:12]4[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[CH:13]=4)[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[C:3]3=[O:20])=[O:33])[CH2:28][CH:27]3[CH2:26][CH:25]([CH2:24][CH:23]([CH2:29]3)[CH2:22]1)[CH2:30]2

Participants

3

Reactant 2

HCID 27718821-Adamantaneacetyl chlorideHCID 67160611HCID 67160611, compound

Product 1

HCID 53236389HCID 53236389, compound

Procedure

The product of Example 163A and 2-(adamantan-1-yl)acetyl chloride were treated using a method similar to that described in Example 1C to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.24 (s, 1H), 8.39-8.42 (m, 1H), 7.88-8.01 (m, 2H), 7.75 (dd, J=6.9, 2.1 Hz, 1H), 7.29-7.35 (m, 3H), 3.56 (s, 1H), 2.33 (s, 2H), 2.32 (s, 3H), 2.05 (d, J=3.0 Hz, 2H), 1.93-1.97 (m, 3H), 1.54-1.72 (m, 12H); MS (APCI+) M/Z 442 (M+H)+.

Sources & evidence

ORD record
ord-31b3eeab6eb646bbb4bd2149c08319de
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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