Potassium Carbonate → HCID 23171553, compound

HRID 863692Notes

Reaction equation

HRID 863692 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:39][CH2:38][N:13]2[C:14]3[C:19]([C:20]([C:21]4[C:22](=[O:37])O[C:24](=[O:36])[C:25]=4[C:26]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]([CH3:35])[CH:27]=4)=[C:12]2[CH2:11]1)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:41][OH:42].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:39][CH2:38][N:13]2[C:14]3[C:19]([C:20]([C:21]4[C:22](=[O:37])[N:41]([OH:42])[C:24](=[O:36])[C:25]=4[C:26]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]([CH3:35])[CH:27]=4)=[C:12]2[CH2:11]1)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 21654380HCID 21654380, compound

Product 1

HCID 23171553HCID 23171553, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 400 mg of 3-[8-[(t-butoxyformamido)methyl]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)furan-2,5-dione in 50 ml of dimethylformamide and 50 ml of water was treated with 2.5 g of hydroxylamine hydrochloride and 2.5 g of potassium carbonate and the solution obtained was heated to 100° C. The solvents were evaporated and the residue was dissolved in dichloromethane, washed with water and dried. The solvent was removed under reduced pressure and the residue was crystallized from ethyl acetate/petroleum ether to give 190 mg of 3-[8-[(t-butoxyformamido)methyl]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-1-hydroxy-4-(1-methyl-3-indolyl)pyrrole-2,5-dione of melting point 238°-240° C.

Workup

  1. customthe solution obtained
  2. customThe solvents were evaporated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washwashed with water
  5. customdried
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was crystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-d1f7e128aa5c459982fb1449c9ab6eee
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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