Choline → N,N,N-Trimethyl-N-(2-hydroxyethyl)-ammonium 1-cyclopropyl-6,8-difluoro-7-[3-(1,2,4-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 1742961Notes

Reaction equation

HRID 1742961 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:25])=[C:11]([N:15]4[CH2:19][CH2:18][CH:17]([N:20]5[CH:24]=[N:23][CH:22]=[N:21]5)[CH2:16]4)[C:12]=3[F:14])[C:7](=[O:26])[C:6]([C:27]([OH:29])=[O:28])=[CH:5]2)[CH2:3][CH2:2]1.[OH:30][CH2:31][CH2:32][N+:33]([CH3:36])([CH3:35])[CH3:34]>CO.O>[CH3:34][N+:33]([CH3:36])([CH3:35])[CH2:32][CH2:31][OH:30].[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:25])=[C:11]([N:15]4[CH2:19][CH2:18][CH:17]([N:20]5[CH:24]=[N:23][CH:22]=[N:21]5)[CH2:16]4)[C:12]=3[F:14])[C:7](=[O:26])[C:6]([C:27]([O-:29])=[O:28])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 305CholineHCID 190059571-Cyclopropyl-6,8-difluoro-7-[3-(1,2,4-triazol-1-yl) pyrrolidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 19006001N,N,N-Trimethyl-N-(2-hydroxyethyl)-ammonium 1-cyclopropyl-6,8-difluoro-7-[3-(1,2,4-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of 100.25 mg (0.25 mmol) of 1-cyclopropyl-6,8-difluoro-7-[3-(1,2,4-triazol-1-yl) pyrrolidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid in 0.625 ml of methanol and 0.2 ml of water was added at room temperature slowly 0.075 ml of 45% choline in methanol. The solution was stirred at room temperature for an additional hour and after being through a cotton filter, the supernatant was evaporated to dryness under reduced pressure (30° C.). The residue was crystallized from acetone-methanol and dried to give 85 mg of off white solid, m.p. 193°-194° C. 1H NMR (CD3OD) δ: 8.61 (s, 1H), 8.42 (bs, 1H), 8.01 (s, 1H), 7.76 (dd, 14Hz, 1.8Hz, 1H), 5.3-5.15 (m, 1H), 4.3-3.75 (m, 7H), 3.5-3.44 (m, 2H), 3.21 (s, 9H), 2.62-2.45 (m, 2H), 1.22-1.02 (m, 4H). Anal. calcd. for C24H30F2N6O4H2O: C, 55.16; H, 6.13; N, 16.07. Found: C, 54.46; H, 5.91; N, 15.82.

Workup

  1. filtrationfilter
  2. customthe supernatant was evaporated to dryness under reduced pressure (30° C.)
  3. customThe residue was crystallized from acetone-methanol
  4. customdried
  5. customto give 85 mg of off white solid, m.p. 193°-194° C

Sources & evidence

ORD record
ord-68f323c7301b46ceaa88a5029dec020d
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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