1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-Amino-1-cyclopropyl-6,8-difluoro-7-[3-(4-methyl-1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4,dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1742951Notes

Reaction equation

HRID 1742951 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.Cl.[CH3:23][C:24]1[N:25]=[N:26][N:27]([CH:29]2[CH2:33][CH2:32][NH:31][CH2:30]2)[CH:28]=1.C1CCN2C(=NCCC2)CC1>C(#N)C>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:31]2[CH2:32][CH2:33][CH:29]([N:27]3[CH:28]=[C:24]([CH3:23])[N:25]=[N:26]3)[CH2:30]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 190059493-(4-Methyl-1,2,3-triazol-1-yl)pyrrolidine hydrochloride

Product 1

HCID 190059585-Amino-1-cyclopropyl-6,8-difluoro-7-[3-(4-methyl-1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4,dihydro-4-oxoquinoline-3-carboxylic acidYield 46.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (298 mg, 1 mmol) was reacted with 470 mg (2.5 mmol) of 3-(4-methyl-1,2,3-triazol-1-yl)pyrrolidine hydrochloride in the presence of 380 mg (2.5 mmol) of DBU in 20 ml of dry acetonitrile for two days under reflux conditions and the atmosphere of nitrogen. The yellow suspension was then evaporated to dryness and to the residue water was added. The yellow solid was filtered and crystallized repeatedly (3x) with acetonitrile to free the product from the unreacted starting material. After drying, 200 mg of the desired product was obtained, m.p. 271°-272.5° C. 1H NMR (TFA) δ: 9.15 (s, 1H), 8.4 (s, 1H), 5.8-5.6 (m, 1H), 4.8-4.05 (m, 5H), 3.0-2.7 (m, 2H), 2.67 (s, 3H), 1.65-1.2 (m, 4H). Anal. calcd. for C20H20F2N6O3.1/2 H2O: C, 54.67; H, 4.82; N, 19.12. Found: C, 54.91; H, 4.69; N, 18.76.

Workup

  1. customThe yellow suspension was then evaporated to dryness and to the residue water
  2. additionwas added
  3. filtrationThe yellow solid was filtered
  4. customcrystallized repeatedly (3x) with acetonitrile
  5. customAfter drying

Sources & evidence

ORD record
ord-48e5c61947824e68a15640f005732a71
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

Loading…