Methanol → HCID 19696441, compound

HRID 863700Notes

Reaction equation

HRID 863700 reaction equation
[C:1]([O:4][CH2:5][CH:6]1[CH2:34][CH2:33][N:9]2[C:10]3[C:15]([C:16]([C:17]4[C:18](=O)[O:19][C:20](=[O:31])[C:21]=4[C:22]4[C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=5[O:24][CH:23]=4)=[C:8]2[CH2:7]1)=[CH:14][CH:13]=[CH:12][CH:11]=3)(=[O:3])[CH3:2].C[Si](C)(C)[NH:37][Si](C)(C)C.CO>C(Cl)(Cl)Cl>[C:1]([O:4][CH2:5][CH:6]1[CH2:34][CH2:33][N:9]2[C:10]3[C:15]([C:16]([C:17]4[C:18](=[O:19])[NH:37][C:20](=[O:31])[C:21]=4[C:22]4[C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=5[O:24][CH:23]=4)=[C:8]2[CH2:7]1)=[CH:14][CH:13]=[CH:12][CH:11]=3)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887Methanol4×HCID 13838Hexamethyldisilazane3×HCID 19696359HCID 19696359, compound

Product 1

HCID 19696441HCID 19696441, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 1.0 g of 3-[8-(acetoxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(3-benzofuranyl)furan-2,5-dione in 100 ml of chloroform was treated with 13.8 ml of hexamethyldisilazane and 2.73 ml of methanol and the solution obtained was heated to 50° C. while stirring under a nitrogen atmosphere for 6 hours. An additional 13.8 ml of hexamethyldisilazane and 2.73 ml of methanol were added and the heating was continued for 16 hours. Two more additions of the same quantities of hexamethyldisilazane and methanol were effected and the temperature of the mixture was held at 50° C. for an additional 24 hours. Then, 20 ml of methanol were added and the mixture was heated to reflux for 15 minutes, cooled and concentrated. The precipitate was filtered off and triturated in succession with ethyl acetate and methanol. There were obtained 630 mg of 3-[8-(acetoxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(3-benzofuranyl)-1H-pyrrole-2,5-dione of melting point 234°-237° C.

Workup

  1. customthe solution obtained
  2. waitthe heating was continued for 16 hours
  3. waitthe temperature of the mixture was held at 50° C. for an additional 24 hours
  4. temperaturethe mixture was heated
  5. temperatureto reflux for 15 minutes
  6. temperaturecooled
  7. concentrationconcentrated
  8. filtrationThe precipitate was filtered off
  9. customtriturated in succession with ethyl acetate and methanol

Sources & evidence

ORD record
ord-b990de84202444dc97d99027bbdf7d71
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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