1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 10619467, compound

HRID 2249244Notes

Reaction equation

HRID 2249244 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11](F)[C:12]=3[O:14][CH3:15])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.C(OC([NH:29][C@H:30]1[C@@H:34]([CH3:35])[CH2:33][NH:32][CH2:31]1)=O)(C)(C)C.C1CCN2C(=NCCC2)CC1>C(#N)C>[NH2:29][C@H:30]1[C@@H:34]([CH3:35])[CH2:33][N:32]([C:11]2[C:12]([O:14][CH3:15])=[C:13]3[C:8]([C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[CH:9][C:10]=2[F:17])[CH2:31]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 70194651-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acidHCID 11138119(3S,4S)-3-(Boc-amino)-4-methylpyrrolidine

Product 1

HCID 10619467HCID 10619467, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid (200 mg), cis-3-t-butoxycarbonylamino-4-methylpyrrolidine (150 mg), DBU (110 mg) and anhydrous acetonitrile (3 ml) was refluxed for 5 hours. After cooling, the resulting precipitate was collected by filtration. This precipitate was added to the mixture of concentrated hydrochloric acid-methanol (1:1, 6 ml) and stirred for 1.5 hours at room temperature. The reaction mixture was neutralized by concentrated aqueous ammonia and allowed to stand in the refrigerator. The resulting crystals were collected by filtration and washed with cold water to give the title compound (90 mg) as colorless prisms, mp 185°-188° C. (decompd.).

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperatureAfter cooling
  3. filtrationthe resulting precipitate was collected by filtration
  4. additionThis precipitate was added to the mixture of concentrated hydrochloric acid-methanol (1:1, 6 ml)
  5. filtrationThe resulting crystals were collected by filtration
  6. washwashed with cold water

Sources & evidence

ORD record
ord-719e0260996344e4954586963dcb8e2a
Source dataset
uspto-grants-1991_08
Patent number
US05043450

Reaction notes

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