Pyridine → HCID 53237062, compound

HRID 469521Notes

Reaction equation

HRID 469521 reaction equation
[NH2:1][N:2]1[C:7](=[O:8])[C:6]2[N:9]=[CH:10][CH:11]=[CH:12][C:5]=2[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:3]1.N1C=CC=CC=1.[C:25]12([CH2:35][C:36](Cl)=[O:37])[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]3)[CH2:26]1)[CH2:32]2>C(Cl)Cl.CCOC(C)=O>[C:25]12([CH2:35][C:36]([NH:1][N:2]3[C:7](=[O:8])[C:6]4[N:9]=[CH:10][CH:11]=[CH:12][C:5]=4[C:4]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)=[N:3]3)=[O:37])[CH2:32][CH:31]3[CH2:30][CH:29]([CH2:28][CH:27]([CH2:33]3)[CH2:26]1)[CH2:34]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 27718821-Adamantaneacetyl chlorideHCID 67159892HCID 67159892, compound

Product 1

HCID 53237062HCID 53237062, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 7B (34.8 mg, 0.146 mmol), pyridine (0.014 mL, 0.18 mmol), and (adamantan-1-yl)acetyl chloride (35.2 mg, 0.165 mmol) in CH2Cl2 (0.45 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 (3% MeOH/CH2Cl2) to give the title compound (43.9 mg, 0.106 mmol) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 11.35 (s, 1H), 9.15 (dd, 1H), 8.16 (dd, 1H), 7.94 (dd, 1H), 7.65-7.54 (m, 5H), 2.08 (s, 2H), 1.95 (s, 3H), 1.74-1.53 (m, 12H); MS (DCI) M/Z 432.2 (M+NH4).

Workup

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

Sources & evidence

ORD record
ord-91dc3ef10938467b8638dc2c2f6d18e9
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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