1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-Amino-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 1742955Notes

Reaction equation

HRID 1742955 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.[N:23]1([CH:28]2[CH2:31][NH:30][CH2:29]2)[CH:27]=[CH:26][N:25]=[N:24]1.C1CCN2C(=NCCC2)CC1>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:30]2[CH2:31][CH:28]([N:23]3[CH:27]=[CH:26][N:25]=[N:24]3)[CH2:29]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[CH2:16][CH2:17]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 190059921-(azetidin-3-yl)-1H-1,2,3-triazole hydrochloride

Product 1

HCID 190060245-Amino-1-cyclopropyl-6,8-difluoro-7-[3-(1,2,3-triazol-1-yl)azetidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 75 mg (0.25 mmol) of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and 3-(1,2,3-triazol-1-yl)azetidine hydrochloride (99.7 mg, 0.625 mmol) in 3 ml of pyridine in the presence of 95 mg of DBU was heated at 75° C. overnight. The resulting suspension was evaporated to dryness and to the residue, water was added and the separated yellow solid was collected (99 mg, 98%), m.p. >330° C. (dec). 1H NMR (TFA) δ: 9.1 (s, 1H), 8.74 (s, 1H), 8.6 (s, 1H), 6.2-5.98 (m, 1H), 5.55-5.05 (m, 4H), 4.45-4.15 (m, 1H), 1.65-1.2 (m, 4H). Anal. calcd. for C18H16F2N6O3 : C, 53.74; H, 4.01; N, 20.88. Found: C, 53.63; H, 3.99; N, 20.20.

Workup

  1. customThe resulting suspension was evaporated to dryness and to the residue, water
  2. additionwas added
  3. customthe separated yellow solid was collected (99 mg, 98%), m.p. >330° C. (dec)

Sources & evidence

ORD record
ord-258adb8d76c9465fb31424d4193ac3a1
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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