Benzylamine → HCID 131728470, compound

HRID 1172499Notes

Reaction equation

HRID 1172499 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]([C:13]1[CH:14]=[C:15]([CH3:35])[C:16]2[O:22][C:21]3[C:23]([Cl:31])=[CH:24][C:25]([NH:27][CH2:28][CH2:29]Cl)=[CH:26][C:20]=3[CH2:19][S:18](=[O:33])(=[O:32])[C:17]=2[CH:34]=1)=[O:12]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CO>[CH3:9][O:10][C:11]([C:13]1[CH:14]=[C:15]([CH3:35])[C:16]2[O:22][C:21]3[C:23]([Cl:31])=[CH:24][C:25]([NH:27][CH2:28][CH2:29][NH:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:26][C:20]=3[CH2:19][S:18](=[O:32])(=[O:33])[C:17]=2[CH:34]=1)=[O:12]

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 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 131728470HCID 131728470, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

Benzyl amine (1.08 g, 10.08 mmol) and tetrabutylammonium iodide (0.02 g, 0.054 mmol) were added to a suspension of the carboxylic acid of Example 56k (0.86 g, 2.0677 mmol) in methanol (8 mL) under nitrogen, in a pressure reactor vessel and heated to 110° C. for 4 h. The reaction mixture was concentrated (oily residue), treated with methanolic HCl (25 mL) and refluxed overnight. It was concentrated, treated with an aqueous sodium bicarbonate solution to pH 8 and extracted with chloroform. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, 1% methanol/chloroform) to obtain the title compound. Yield: 0.56 g, (54%); 1H NMR (CDCl3): δ 2.62 (s, 3H, CH3), 2.95 (t, 2H CH2), 3.2 (m, 2H, CH2), 3.83 (s, 2H, CH2), 3.9 (s, 2H, CH2), 4.95 (s, 1H, NH), 6.5 (s, 1H, Ar), 6.53 (s, 1H, Ar), 7.4 (m, 5H, Ar), 8.1 (s, 1H, Ar), 8.47 (s, 1H, Ar); MS: m/e (ES+) 501 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated (oily residue)
  2. additiontreated with methanolic HCl (25 mL)
  3. temperaturerefluxed overnight
  4. concentrationIt was concentrated
  5. additiontreated with an aqueous sodium bicarbonate solution to pH 8
  6. extractionextracted with chloroform
  7. washThe organic layer was washed with water, brine
  8. customdried
  9. concentrationconcentrated
  10. custompurified

Sources & evidence

ORD record
ord-fca62eafe49240a2bc8c157adce468f3
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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