1-Adamantaneacetyl chloride → HCID 67160092, compound

HRID 469584Notes

Reaction equation

HRID 469584 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:18].[C:19]12([CH2:29][C:30](Cl)=[O:31])[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[CH2:20]1)[CH2:26]2>>[C:19]12([CH2:29][C:30]([NH:1][N:2]3[N:11]=[C:10]([CH:12]4[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]4)[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[C:3]3=[O:18])=[O:31])[CH2:26][CH:25]3[CH2:24][CH:23]([CH2:22][CH:21]([CH2:27]3)[CH2:20]1)[CH2:28]2

Participants

3

Reactant 2

HCID 27718821-Adamantaneacetyl chlorideHCID 67160451HCID 67160451, compound

Product 1

HCID 67160092HCID 67160092, compound

Procedure

The product of Example 74A and 2-(adamantan-1-yl)acetyl chloride were processed using a method similar to that described in Example 1C, and purified by preparative HPLC [Phenomenex Luna C8(2) 5 um 100 Å AXIA column (30 mm×75 mm); a gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B) was used, at a flow rate of 50 mL/min (0-0.5 min 10% A, 0.5-7.0 min linear gradient 10-95% A, 7.0-10.0 min 95% A, 10.0-12.0 min linear gradient 95-10% A)] to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.10 (s, 1H), 8.34 (d, J=7.9 Hz, 1H), 8.11 (d, J=8.1 Hz, 1H), 7.97-8.01 (m, 1H), 7.89 (t, J=7.5 Hz, 1H), 3.21-3.40 (m, 1H), 1.39-1.98 (m, 26H), 1.13-1.27 (m, 1H); MS (ESI) m/z 420 (M+H)+.

Workup

  1. custompurified by preparative HPLC [Phenomenex Luna C8(2) 5 um 100 Å AXIA column (30 mm×75 mm)
  2. customwas used, at a flow rate of 50 mL/min (0-0.5 min 10% A, 0.5-7.0 min linear gradient 10-95% A, 7.0-10.0 min 95% A, 10.0-12.0 min linear gradient 95-10% A)

Sources & evidence

ORD record
ord-2c2e91664e3c41649fee442e87cdbdfa
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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