2-Pyridineethanamine → HCID 131728465, compound

HRID 1927482Notes

Reaction equation

HRID 1927482 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[CH3:10][O:11][C:12]([C:14]1[CH:15]=[C:16]([CH3:36])[C:17]2[O:23][C:22]3[C:24]([Cl:32])=[CH:25][C:26]([NH:28][CH2:29][CH2:30]Cl)=[CH:27][C:21]=3[CH2:20][S:19](=[O:34])(=[O:33])[C:18]=2[CH:35]=1)=[O:13]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CO>[CH3:10][O:11][C:12]([C:14]1[CH:15]=[C:16]([CH3:36])[C:17]2[O:23][C:22]3[C:24]([Cl:32])=[CH:25][C:26]([NH:28][CH2:29][CH2:30][NH:1][CH2:2][CH2:3][C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=4)=[CH:27][C:21]=3[CH2:20][S:19](=[O:33])(=[O:34])[C:18]=2[CH:35]=1)=[O:13]

Participants

5

Reactant 2

HCID 759192-PyridineethanamineHCID 1317284464-Chloro-2-(2-chloro-ethylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]-cycloheptene-8-carboxylic acid methyl ester

Product 1

HCID 131728465HCID 131728465, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

2-(2-Aminoethyl)pyridine (8.13 mmol) and tetrabutylammonium iodide (0.010 g, 0.027 mmol) were sequentially added with stirring to a solution of the carboxylic acid of Example 56k (0.7 g, 1.62 mmol) in dry methanol (10 mL). The reaction mixture was stirred at 110° C. for 7 h in an atmosphere of nitrogen. It was concentrated and treated with a methanolic HCl solution (10 mL), refluxed overnight, concentrated, treated water and 10% aqueous sodium bicarbonate solution to pH 7. The solid that precipitated was filtered, washed with water, dried and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound as a white solid. Yield: 0.225 g, (26.81%). 1H NMR (DMSO-d6): δ 2.70 (s, 3H, CH3), 3.0-3.10 (m, 6H, 3CH2), 3.40-3.55 (m, 2H, CH2), 3.90 (s, 3H, OCH3), 5.20 (s, 2H, CH2), 6.45 (t, 1H, NH), 6.80 (s, 1H, Ar), 6.83 (s, 1H, Ar), 7.30-7.50 (m, 3H, Ar), 7.80 (t, 1H, Ar), 8.20 (s, 1H, Ar), 8.25 (s, 1H, Ar); MS (CI+): m/e 516 (M+1).

Workup

  1. concentrationIt was concentrated
  2. additiontreated with a methanolic HCl solution (10 mL)
  3. temperaturerefluxed overnight
  4. concentrationconcentrated
  5. additiontreated water and 10% aqueous sodium bicarbonate solution to pH 7
  6. customThe solid that precipitated
  7. filtrationwas filtered
  8. washwashed with water
  9. customdried
  10. custompurified

Sources & evidence

ORD record
ord-942eeea0b61f47c582ccc93f37478bb4
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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