1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 67883129, compound

HRID 2081567Notes

Reaction equation

HRID 2081567 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9]3=[C:10]([CH2:13][C@H:14]([CH3:15])[N:8]3[CH:7]=[C:6]([C:16]([OH:18])=[O:17])[C:5]2=[O:19])[C:11]=1F.[ClH:20].Cl.NN1CCCC1.C1C[CH2:37][N:36]2C(=[N:32][CH2:33][CH2:34][CH2:35]2)CC1>CN(C)P(=O)(N(C)C)N(C)C>[ClH:20].[F:1][C:2]1[CH:3]=[C:4]2[C:9]3=[C:10]([CH2:13][CH:14]([CH3:15])[N:8]3[CH:7]=[C:6]([C:16]([OH:18])=[O:17])[C:5]2=[O:19])[C:11]=1[N:36]1[CH2:35][CH2:34][CH:33]([NH2:32])[CH2:37]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10491907HCID 10491907, compoundHCID 18985368Pyrrolidin-1-amine--hydrogen chloride (1/2)

Product 1

HCID 67883129HCID 67883129, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

To 7 g of (+)-8,9-difluoro-2-(S)-methyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid obtained in Example 5 were added 21 g of aminopyrrolidine dihydrochloride, 40 ml of 1,8-diazabicyclo[5,4,0]-7-undecene (DBU) and 70 ml of hexamethylphosphoric triamide, and allowed to react in an oil bath at 120°-130° C. for 2 hours. The solvent was evaporated off under reduced pressure, and the residue was dissolved in 100 ml of 2% aqueous hydrochloric acid. Insoluble matters were filtered off, the filtrate was concentrated, and the residue was recrystallized from ethanol-water to obtain (+)-8-fluoro-2-methyl-9-(3-amino-1-pyrrolidyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride.

Workup

  1. customto react in an oil bath at 120°-130° C. for 2 hours
  2. customThe solvent was evaporated off under reduced pressure
  3. dissolutionthe residue was dissolved in 100 ml of 2% aqueous hydrochloric acid
  4. filtrationInsoluble matters were filtered off
  5. concentrationthe filtrate was concentrated
  6. customthe residue was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-1933d3e55a42466b8b4629691ebb9dff
Source dataset
uspto-grants-1993_02
Patent number
US05185337

Reaction notes

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