Triethylamine → 7-[3-(Tert-butyloxycarbonylamino)pyrrolidin-1-yl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carbonitrile

HRID 622789Notes

Reaction equation

HRID 622789 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]#[N:19])=[CH:5]2)[CH2:3][CH2:2]1.[C:20]([O:24][C:25]([NH:27][CH:28]1[CH2:32][CH2:31][NH:30][CH2:29]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C(N(CC)CC)C>C(#N)C>[C:20]([O:24][C:25]([NH:27][CH:28]1[CH2:32][CH2:31][N:30]([C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:17])[C:6]([C:18]#[N:19])=[CH:5][N:4]3[CH:1]3[CH2:2][CH2:3]3)=[CH:9][C:10]=2[F:16])[CH2:29]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 143023471-Cyclopropyl-3-cyano-1,4-dihydro-4-oxo-6,7,8-trifluoroquinoline

Product 1

HCID 143023487-[3-(Tert-butyloxycarbonylamino)pyrrolidin-1-yl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carbonitrileYield 93.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carbonitrile (5.04 g) and 3-(tertbutyloxycarbonylamino)pyrrolidine (3.96 g) were combined in acetonitrile (48 ml). The mixture was heated to reflux at which point all the solids dissolved. After refluxing for 15-20 minutes a precipitate formed. Stirring was continued at reflux overnight (22 hours). Triethylamine (6 ml) was then added and refluxing continued another seven hours before cooling to room temperature. The solid was collected by filtration and then washed with acetonitrile (15 ml) followed by a solution of triethylamine (5 ml) in acetonitrile (5 ml). The solid was dried under vacuum at 50° C. to give 7-[3-(tert-butyloxycarbonylamino)pyrrolidin-1-yl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carbonitrile (7.65 g, 93%), mp 249°-250° C. (dec).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux at which point all the solids
  3. dissolutiondissolved
  4. temperatureAfter refluxing for 15-20 minutes a precipitate
  5. customformed
  6. temperatureat reflux overnight (22 hours)
  7. temperaturerefluxing
  8. filtrationThe solid was collected by filtration
  9. washwashed with acetonitrile (15 ml)
  10. customThe solid was dried under vacuum at 50° C.

Sources & evidence

ORD record
ord-fa1aed3d24994ae8bc6394d249799178
Source dataset
uspto-grants-1988_09
Patent number
US04772706

Reaction notes

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