Methanol → HCID 22850696, compound

HRID 486778Notes

Reaction equation

HRID 486778 reaction equation
C[Si](C)(C)[NH:3][Si](C)(C)C.CO.[ClH:12].[CH3:13][N:14]1[CH2:46][C@@H:45]2[C@H:16]([CH2:17][C:18]3[N:19]([CH2:44]2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=2[C:26]=3[C:27]2[C:28](=[O:43])[O:29][C:30](=O)[C:31]=2[C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]([CH3:41])[CH:33]=2)[CH2:15]1>CN(C=O)C.C(OCC)(=O)C>[ClH:12].[CH3:13][N:14]1[CH2:46][C@@H:45]2[C@H:16]([CH2:17][C:18]3[N:19]([CH2:44]2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=2[C:26]=3[C:27]2[C:28](=[O:43])[NH:3][C:30](=[O:29])[C:31]=2[C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]([CH3:41])[CH:33]=2)[CH2:15]1

Participants

6

Reactant 3

HCID 887Methanol2×HCID 13838Hexamethyldisilazane2×HCID 86747650HCID 86747650, compound

Product 1

HCID 22850696HCID 22850696, compoundYield 58.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 1.21 g of 1,1,1,3,3,3-hexamethyldisilazane and 132 mg of methanol was added to a solution of 400 mg of trans-3-(2,3,3a,4,11,11a-hexahydro-2-methyl-1H-pyrrolo[3',4':4,5]-pyrido[1,2-a]indol-10-yl)-4-(1-methyl-3-indolyl)furan-2,5-dione hydrochloride in 30 ml of DMF and stirred for 48 hours. A further 100 mg of methanol and 0.95 g of 1,1,1,3,3,3-hexamethyldisilazane were added, the mixture was heated to 45° C. for 2 hours and then left to stand at room temperature. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate, dichloromethane and methanol. The solution obtained was washed with saturated sodium bicarbonate solution and the organic layer was concentrated. A saturated solution of hydrogen chloride in ethyl acetate was added and the precipitate obtained was filtered off. The solid was suspended in water and stirred, then filtered off and dried. The solid obtained was suspended in ethyl acetate and stirred, then filtered off and dried to give 235 mg of trans-3-(2,3,3a,4,11,11a-hexahydro-2-methyl-1H-pyrrolo[3',4':4,5]pyrido[1,2-a]indol-10-yl)-4 -(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione hydrochloride of melting point >330° C.

Workup

  1. waitleft
  2. customto stand at room temperature
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. customThe solution obtained
  6. washwas washed with saturated sodium bicarbonate solution
  7. concentrationthe organic layer was concentrated
  8. additionA saturated solution of hydrogen chloride in ethyl acetate was added
  9. customthe precipitate obtained
  10. filtrationwas filtered off
  11. stirringstirred
  12. filtrationfiltered off
  13. customdried
  14. customThe solid obtained
  15. stirringstirred
  16. filtrationfiltered off
  17. customdried

Sources & evidence

ORD record
ord-7295d5eaae5446a3aa56f609538e96e6
Source dataset
uspto-grants-1994_03
Patent number
US05292747

Reaction notes

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