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

HRID 1742959Notes

Reaction equation

HRID 1742959 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:26])=[C:11]([N:15]4[CH2:19][CH2:18][CH:17]([N:20]5[CH:24]=[C:23]([CH3:25])[N:22]=[N:21]5)[CH2:16]4)[C:12]=3[F:14])[C:7](=[O:27])[C:6]([C:28]([OH:30])=[O:29])=[CH:5]2)[CH2:3][CH2:2]1.[OH-].[CH3:32][N+:33]([CH2:36][CH2:37][OH:38])([CH3:35])[CH3:34]>CO.O>[CH3:32][N+:33]([CH3:35])([CH3:34])[CH2:36][CH2:37][OH:38].[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:26])=[C:11]([N:15]4[CH2:19][CH2:18][CH:17]([N:20]5[CH:24]=[C:23]([CH3:25])[N:22]=[N:21]5)[CH2:16]4)[C:12]=3[F:14])[C:7](=[O:27])[C:6]([C:28]([O-:30])=[O:29])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 31255Choline, hydroxideHCID 190059371-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

Product 1

HCID 19005961N,N,N-Trimethyl-N-(2-hydroxyethyl)-ammonium 1-cyclopropyl-6,8-difluoro-7-[3-(4-methyl-1,2,3-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 1-cyclopropyl-6,8-difluoro-7-[3-(4-Methyl-1,2,3-triazol-1-yl)pyrrolidine-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (415.5 mg, 1 mmol) in 2.5 ml of methanol and 0.8 ml water at room temperature was added slowly 0.31 ml Of 45% N,N,N-trimethyl-2-hydroxyethyl-ammonium hydroxide in methanol (1 mmol). The solution was stirred at room temperature for an additional hour. This was filtered and the supernatant was evaporated under reduced pressure at 30° C. The residue was crystallized from acetone-methanol to yield after drying 420 mg of off-white solid, m.p. 188.7°-190.7° C. 1H NMR (D20) δ: 8.44 (s, 1H), 7.84 (bs, 1H), 7.62 (bd, 13.9Hz, 1H), 5.43-5.22 (m, 1H), 4.35-3.62 (m, 7H), 3.52 (t, 2H), 3.21 (s, 9H), 2.73-2.16 (m, 2H) 2.29 (s, 3H), 1.74-0.9 (m, 4H). Anal. calcd. for C25H32F2N6O4 . 1/2 H2O: C, 56.98; H, 6.31; N, 15.94. Found: C, 56.76; H, 6.26; N, 15.43.

Workup

  1. filtrationThis was filtered
  2. customthe supernatant was evaporated under reduced pressure at 30° C
  3. customThe residue was crystallized from acetone-methanol
  4. customto yield
  5. dry with materialafter drying 420 mg of off-white solid, m.p. 188.7°-190.7° C

Sources & evidence

ORD record
ord-1ca23f725fcb4350b1e332ba11f06e57
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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