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

HRID 1742952Notes

Reaction equation

HRID 1742952 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]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.Cl.[CH3:22][C:23]1[N:24]=[N:25][N:26]([CH:29]2[CH2:33][CH2:32][NH:31][CH2:30]2)[C:27]=1[CH3:28].C1CCN2C(=NCCC2)CC1>N1C=CC=CC=1>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:31]4[CH2:32][CH2:33][CH:29]([N:26]5[C:27]([CH3:28])=[C:23]([CH3:22])[N:24]=[N:25]5)[CH2:30]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 190059233-(4,5-Dimethyl-1,2,3-triazol-1-yl)pyrrolidine hydrochloride

Product 1

HCID 190059811-Cyclopropyl-6,8-difluoro-7-[3-(4,5-dimethyl-1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (100 mg, 0.36 mmol) was reacted with 3-(4 , 5-dimethyl-1,2,3-triazol-1-yl)pyrrolidine hydrochloride (182 mg, 0.9 mmol) in 8 ml of dry pyridine in the presence of 137 mg (0.9 mmol) of DBU at 115° C. for five days. The small amount of the solid was filtered off and the supernatant was evaporated to dryness. To the residue, water and a few drops of acetonitrile were added. The solid was collected to afford after drying 125 mg (81%) of the desired product as a gray solid. m.p. 230-232 ° C. (dec). 1H NMR (CDCl3) δ: 8.74 (s, 1H), 7.84 (d, J=13.2Hz, 1H), 5.07-4.8 (m, 1H), 4.4-3.85 (m, 5H), 2.8-2.14 (m, 8H, singlet at 2.29, 6H), 1.4-1.0 (m, 4H). Anal. calcd. for C21H12F2N5O3.1/2 H2O: C, 57.52; H, 4.83; N, 15.97. Found: C, 57.68; H, 4.81; N, 15.68.

Workup

  1. filtrationThe small amount of the solid was filtered off
  2. customthe supernatant was evaporated to dryness
  3. additionTo the residue, water and a few drops of acetonitrile were added
  4. customThe solid was collected
  5. customto afford
  6. dry with materialafter drying 125 mg (81%) of the desired product as a gray solid

Sources & evidence

ORD record
ord-af4f92572db641e6af0764bcc4df1087
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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