Formic Acid → Diisopropyl Ether

HRID 1415940Notes

Reaction equation

HRID 1415940 reaction equation
[NH2:1][C:2]1[C:3]([F:30])=[C:4]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:25])=[C:16]([N:19]4[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20]4)[N:17]=3)[C:12](=[O:26])[C:11]([C:27]([OH:29])=[O:28])=[CH:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[CH:31](O)=O.[CH2:34](O)[CH3:35]>>[CH:34]([O:26][CH:12]([CH3:11])[CH3:13])([CH3:35])[CH3:31].[CH:27]([OH:29])=[O:28].[NH2:1][C:2]1[C:3]([F:30])=[C:4]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:25])=[C:16]([N:19]4[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20]4)[N:17]=3)[C:12](=[O:26])[C:11]([C:27]([OH:29])=[O:28])=[CH:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 702Ethanol2×HCID 11080272HCID 11080272, compound

Product 2

HCID 7914Diisopropyl EtherHCID 69960759HCID 69960759, compound

Procedure

A mixture of 200 mg of 1-(3-amino-2,4-difluorophenyl)-7-[(3S)-3-aminopyrrolidin-1-yl]-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid and 200 mg of formic acid was stirred for about one minute, combined with 200 mg of ethanol and stirred at 90° C. for one minute. The solution was combined with 2 ml of ethanol, stirred at the same temperature for a further 2 minutes, and allowed to stand. The precipitate was collected by filtration and washed with ethanol and then with diisopropyl ether to give 154 mg of the title compound.

Workup

  1. stirringstirred at 90° C. for one minute
  2. stirringstirred at the same temperature for a further 2 minutes
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-0c193f7e13154269b1dd782d07f57275
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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