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

HRID 1742947Notes

Reaction equation

HRID 1742947 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.[N:22]1([CH:27]2[CH2:30][NH:29][CH2:28]2)[CH:26]=[CH:25][N:24]=[N:23]1.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:29]4[CH2:30][CH:27]([N:22]5[CH:26]=[CH:25][N:24]=[N:23]5)[CH2:28]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 190059921-(azetidin-3-yl)-1H-1,2,3-triazole hydrochloride

Product 1

HCID 543333531-Cyclopropyl-6,8-difluoro-7-[3-(1,2,3-triazol-1-yl) azetidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (50 mg, 0.18 mmol) was reacted with 3-(1,2,3-triazol-1-yl) azetidine hydrochloride (72 mg, 0.45 mmol) in 3 ml of dry pyridine in the presence of 68.5 mg (0.45 mmol) of DBU at 80° C. for 16 h. The yellow solution was then evaporated to dryness, water was added to the residue, solid was collected and dried to yield 64 mg (92%) of the desired product. m.p. 315°-316° C. 1H NMR (TFA) δ: 9.26 (s, 1H), 8.75 (d, 1.2Hz, 1H), 8.60 (d, 1.2Hz, 1H), 8.10 (d, 11.8Hz, 1H), 6.35-6.0 (m, 1H), 5.8-5.15 (m, 4H), 4.65-4.3 (m, 1H), 1.9-1.3 (m, 4H). Anal. calcd. for C18H15F2N 5 O3H2O: C, 53.33; H, 4.23; N, 17.28. Found: C, 53.68; H, 4.23; N, 17.28.

Workup

  1. customThe yellow solution was then evaporated to dryness, water
  2. additionwas added to the residue, solid
  3. customwas collected
  4. customdried

Sources & evidence

ORD record
ord-2bef60fd35284caeac303cc0739a28f0
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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