1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 3025928, compound

HRID 2249252Notes

Reaction equation

HRID 2249252 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[CH:16]1[CH2:18][CH2:17]1.C(OC([NH:30][CH:31]1[CH2:35][CH2:34][NH:33][CH2:32]1)=O)(C)(C)C.C1CCN2C(=NCCC2)CC1>C(#N)C>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:33]2[CH2:34][CH2:35][CH:31]([NH2:30])[CH2:32]2)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[CH:16]1[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 105668945-Amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 3025928HCID 3025928, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid (90 mg), 3-t-butoxycarbonylaminopyrrolidine (115 mg), DBU (50 mg) and anhydrous acetonitrile (4 ml) was refluxed for 20 hours. After cooling, the resulting precipitate was collected by filtration and added to concentrated hydrochloric acid-methanol (1:1, 2 ml). The mixture was stirred for 10 minutes at room temperature, then neutralized with concentrated aqueous ammonia, and the precipitate was collected by filtration. A solution of the precipitate in cold water was acidified with concentrated hydrochloric acid below pH 1 and allowed to stand in a refrigerator. The resulting precipitate was collected by filtration and washed with cold diluted aqueous hydrochloric acid to give the title compound (35 mg) as yellow needles, mp 254°-257° C. (decompd.).

Workup

  1. temperaturewas refluxed for 20 hours
  2. temperatureAfter cooling
  3. filtrationthe resulting precipitate was collected by filtration
  4. additionadded to concentrated hydrochloric acid-methanol (1:1, 2 ml)
  5. filtrationthe precipitate was collected by filtration
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with cold diluted aqueous hydrochloric acid

Sources & evidence

ORD record
ord-39aae02ad6c146578a50c6d8d19a580e
Source dataset
uspto-grants-1991_08
Patent number
US05043450

Reaction notes

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