Pyridine → HCID 53237064, compound

HRID 469526Notes

Reaction equation

HRID 469526 reaction equation
[NH2:1][N:2]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][S:11][C:5]=2[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:3]1.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[C:7](=[O:8])[C:6]4[CH:9]=[CH:10][S:11][C:5]=4[C:4]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[N:3]3)=[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 67161596HCID 67161596, compound

Product 1

HCID 53237064HCID 53237064, compoundYield 51.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product from Example 9B (31 mg), pyridine (0.012 mL, 0.15 mmol), and (adamantan-1-yl)acetyl chloride (31 mg, 0.15 mmol) in CH2Cl2 (0.4 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 (10% EtOAc/CH2Cl2) to give the title compound (27.7 mg, 0.066 mmol) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 11.31 (s, 1H), 8.23 (d, J=5.2 Hz, 1H), 7.86-7.78 (m, 3H), 7.65-7.55 (m, 3H), 2.07 (s, 2H), 1.95 (s, 3H), 1.76-1.53 (m, 12H); MS (ESI+) M/Z 420.3 (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 (10% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-1f4459ba999640cb8cd7f79cb51a4c62
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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