Pyridine → HCID 53237063, compound

HRID 469524Notes

Reaction equation

HRID 469524 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[C:9]2[CH:8]3[CH2:15][CH2:16][CH:5]([CH2:6][CH2:7]3)[C:4]=2[C:3]1=[O:17].N1C=CC=CC=1.[C:24]12([CH2:34][C:35](Cl)=[O:36])[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2>C(Cl)Cl.CCOC(C)=O>[C:24]12([CH2:34][C:35]([NH:1][N:2]3[N:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[C:9]4[CH:8]5[CH2:15][CH2:16][CH:5]([CH2:6][CH2:7]5)[C:4]=4[C:3]3=[O:17])=[O:36])[CH2:31][CH:30]3[CH2:29][CH:28]([CH2:27][CH:26]([CH2:32]3)[CH2:25]1)[CH2:33]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 27718821-Adamantaneacetyl chlorideHCID 67160981HCID 67160981, compound

Product 1

HCID 53237063HCID 53237063, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 8C (18.3 mg), pyridine (0.008 mL, 0.10 mmol), and (adamantan-1-yl)acetyl chloride (18.7 mg, 0.088 mmol) in CH2Cl2 (0.35 mL) was stirred for 2 hours, diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4), and filtered. The residue was chromatographed on SiO2 (20% EtOAc/CH2Cl2) to give the title compound (17.6 mg, 0.043 mmol) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 10.95 (s, 1H), 3.40-3.35 (m, 1H), 3.21-3.07 (m, 2H), 1.99 (s, 2H), 1.93 (s, 3H), 1.83-1.72 (m, 4H), 1.72-1.54 (m, 12H), 1.33-1.17 (m, 4H), 1.14 (d, 6H); MS (ESI+) M/Z 410.1 (M+H)+.

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe residue was chromatographed on SiO2 (20% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-9a4d3e04b1c14ca683540eb30f68eb9d
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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