1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 70419665, compound

HRID 580598Notes

Reaction equation

HRID 580598 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[F:18].C(OC([NH:26][C@H:27]1[C@@H:31]([CH3:32])[CH2:30][NH:29][CH2:28]1)=O)(C)(C)C.C1CCN2C(=NCCC2)CC1>C(#N)C>[NH2:26][C@H:27]1[C@@H:31]([CH3:32])[CH2:30][N:29]([C:2]2[CH:11]=[C:10]3[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]3[CH2:12][CH3:13])=[CH:4][C:3]=2[F:18])[CH2:28]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 11138119(3S,4S)-3-(Boc-amino)-4-methylpyrrolidine

Product 1

HCID 70419665HCID 70419665, compoundYield 0.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (1.0 g), cis-3-t-butoxycarbonylamino-4-methylpyrrolidine (0.89 g), DBU (0.62 g) and anhydrous acetonitrile (30 ml) was refluxed for 27 hours. Then, the reacting mixture was treated as described in example 33 and recrystallized from chloroform-methanol-concentrated aqueous ammonia (20:20:1) to give the title compound (0.008 g) as white powder, mp 300~° C. (decompd.).

Workup

  1. temperaturewas refluxed for 27 hours
  2. additionThen, the reacting mixture was treated
  3. customrecrystallized from chloroform-methanol-concentrated aqueous ammonia (20:20:1)

Sources & evidence

ORD record
ord-ad3af17cb2c64ad6bbc0cd20576a25b4
Source dataset
uspto-grants-1988_06
Patent number
US04753953

Reaction notes

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