Cyclopropylamine → HCID 131728464, compound

HRID 1927481Notes

Reaction equation

HRID 1927481 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]([CH3:31])[C:12]2[O:18][C:17]3[C:19]([Cl:27])=[CH:20][C:21]([NH:23][CH2:24][CH2:25]Cl)=[CH:22][C:16]=3[CH2:15][S:14](=[O:29])(=[O:28])[C:13]=2[CH:30]=1)=[O:8]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CO>[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]([CH3:31])[C:12]2[O:18][C:17]3[C:19]([Cl:27])=[CH:20][C:21]([NH:23][CH2:24][CH2:25][NH:4][CH:1]4[CH2:3][CH2:2]4)=[CH:22][C:16]=3[CH2:15][S:14](=[O:28])(=[O:29])[C:13]=2[CH:30]=1)=[O:8]

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 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 131728464HCID 131728464, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

Cyclopropylamine (0.819 g, 1.4 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 (0.59 g, 1.2 mmol) in dry methanol (10 mL). The reaction mixture was stirred at 110° C. for 5 h in an atmosphere of nitrogen. It was concentrated, treated with a methanolic HCl solution (15 mL) and refluxed for 2 h. The reaction mixture was concentrated, treated with an aqueous sodium bicarbonate solution to pH 7, water and extracted with n-butanol. The organic layer was washed with water, brine, dried and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound as a white solid. Yield: 0.120 g, (22%); 1H NMR (DMSO-d6): δ 0.20 (d, 2H, CH2), 0.40 (d, 2H, CH2), 2.10 (m, 1H, CH), 2.60 (s, 3H, CH3), 2.80 (t, 2H, CH2), 3.10 (d, 2H, CH2), 3.90 (s, 3H, OCH3), 5.15 (s, 2H, CH2), 6.10 (t, 1H, NH), 6.70 (s, 1H, Ar), 6.72 (s, 1H, Ar), 8.10 (s, 1H, Ar), 8.20 (s, 1H, Ar); MS: m/e (CI+) 451 (M+1).

Workup

  1. concentrationIt was concentrated
  2. additiontreated with a methanolic HCl solution (15 mL)
  3. temperaturerefluxed for 2 h
  4. concentrationThe reaction mixture was concentrated
  5. additiontreated with an aqueous sodium bicarbonate solution to pH 7, water
  6. extractionextracted with n-butanol
  7. washThe organic layer was washed with water, brine
  8. customdried
  9. custompurified

Sources & evidence

ORD record
ord-f1b2b955e60f489dadb8aec7627b0cdf
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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