Methanesulfonic Acid → 1-Cyclopropyl-6,8-difluoro-7-[3-(1,2,4-triazol-1-yl) pyrrolidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid methanesulfonate

HRID 1742957Notes

Reaction equation

HRID 1742957 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.[CH3:30][S:31]([OH:34])(=[O:33])=[O:32]>C(Cl)(Cl)Cl>[CH3:30][S:31]([OH:34])(=[O:33])=[O:32].[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)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 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 867480961-Cyclopropyl-6,8-difluoro-7-[3-(1,2,4-triazol-1-yl) pyrrolidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid methanesulfonate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1-cyclopropyl-6,8-difluoro-7-[3-(1,2,4-triazol -1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (20 mg, 0.05 mmol) was dissolved in 2 ml of chloroform and to this was added 4 ml of methanesulfonic acid in chloroform. The suspension formed was stirred at room temperature for five hr. The solid was collected to yield 12 mg of white solid after drying very well in the oven, m.p. 208.5°-210° C. 1H NMR (CD3OD) δ: 9.54 (s, 1H), 8.78 (s, 1H), 8.64 (s, 1H), 7.81 (dd, 13.8, 2.3Hz, 1H), 5.47-5.3 (m, 1H), 4.5-3.8 (m, 5H), 2.88-2.5 (m, 2H), 2.7 (s, 3H), 1.4-1.1 (m, 4H). Anal. calcd. for C20H21F2N5O6S . H2O: C, 46.60; H, 4.50; N, 13.59.Found: C, 46.75; H, 4.38; N, 13.51.

Workup

  1. customThe suspension formed
  2. customThe solid was collected

Sources & evidence

ORD record
ord-2b08be761698415f88627290a75c638f
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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