Methanol → HCID 131728506, compound

HRID 1927526Notes

Reaction equation

HRID 1927526 reaction equation
[CH2:1]([NH2:7])[CH:2]1[O:6][CH2:5][CH2:4][CH2:3]1.Cl[CH2:9][CH2:10][N:11]([CH2:34][CH2:35]Cl)[C:12]1[CH:32]=[C:31]([Cl:33])[C:15]2[O:16][C:17]3[C:26]([CH3:27])=[CH:25][C:24]([C:28]([OH:30])=[O:29])=[CH:23][C:18]=3[S:19](=[O:22])(=[O:21])[CH2:20][C:14]=2[CH:13]=1.[CH3:37]O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:37][O:30][C:28]([C:24]1[CH:25]=[C:26]([CH3:27])[C:17]2[O:16][C:15]3[C:31]([Cl:33])=[CH:32][C:12]([N:11]4[CH2:10][CH2:9][N:7]([CH2:1][CH:2]5[CH2:3][CH2:4][CH2:5][O:6]5)[CH2:35][CH2:34]4)=[CH:13][C:14]=3[CH2:20][S:19](=[O:22])(=[O:21])[C:18]=2[CH:23]=1)=[O:29]

Participants

5

Reactant 3

HCID 887MethanolHCID 253298TetrahydrofurfurylamineHCID 1317284742-[Bis-(2-chloroethyl)amino]-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]-cycloheptene-8-carboxylic acid

Product 1

HCID 131728506HCID 131728506, compound

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Conditions

Temperature
110 °C

Procedure

Tetrahydrofurfurylamine (0.776 mL, 7.5 mmol) was added to a mixture of Example 102j (0.6 g, 1.25 mmol) and tetrabutylammonium iodide (0.004 g) in methanol (5 mL), under argon, in a pressure reactor vessel heated at 110° C. for 5 h. The reaction mixture was cooled, concentrated, treated with methanolic HCl (15 mL) and refluxed for 4 h. The reaction mixture was cooled, concentrated and extracted with n-butanol. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound as an off-white solid. Yield: 0.332 g, (51%); 1H NMR (DMSO-d6): δ 1.5 (m, 2H, CH2), 1.78 (m, 2H, CH2), 1.92 (m, 2H, CH2), 2.67 (s, 3H, CH3), 3.19 (t, 4H, 2CH2), 3.63 (q, 1H, CH2), 3.78 (q, 1H, CH2), 3.9 (s, 3H, OCH3), 3.99 (m, 2H, CH2), 5.17 (s, 2H, CH2), 7.6 (d, 1H, Ar), 7.15 (d, 1H, Ar), 8.11 (s, 1H, Ar), 8.16 (s, 1H, Ar); MS: m/e (ES+) 522 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. additiontreated with methanolic HCl (15 mL)
  4. temperaturerefluxed for 4 h
  5. temperatureThe reaction mixture was cooled
  6. concentrationconcentrated
  7. extractionextracted with n-butanol
  8. washThe organic layer was washed with water, brine
  9. customdried
  10. concentrationconcentrated
  11. custompurified

Sources & evidence

ORD record
ord-addc33cdbf3945599ae19e82a30f5956
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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