Dimethylformamide → Diisopropyl Ether

HRID 1415945Notes

Reaction equation

HRID 1415945 reaction equation
[CH3:1][N:2](C)[CH:3]=[O:4].[NH2:6][C:7]1[C:8]([F:35])=[C:9]([N:14]2[C:23]3[C:18](=[CH:19][C:20]([F:30])=[C:21]([N:24]4[CH2:28]C[C@H:26](N)[CH2:25]4)[N:22]=3)[C:17](=[O:31])[C:16]([C:32]([OH:34])=[O:33])=[CH:15]2)[CH:10]=[CH:11][C:12]=1[F:13].[CH:36]([O:39][CH:40]([CH3:42])[CH3:41])([CH3:38])[CH3:37]>C(O)=O>[CH:36]([O:39][CH:40]([CH3:42])[CH3:41])([CH3:38])[CH3:37].[NH2:6][C:7]1[C:8]([F:35])=[C:9]([N:14]2[C:23]3[C:18](=[CH:19][C:20]([F:30])=[C:21]([N:24]4[CH2:25][CH2:26][C@H:1]([NH:2][CH:3]=[O:4])[CH2:28]4)[N:22]=3)[C:17](=[O:31])[C:16]([C:32]([OH:34])=[O:33])=[CH:15]2)[CH:10]=[CH:11][C:12]=1[F:13]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 7914Diisopropyl EtherHCID 11080272HCID 11080272, compound

Product 2

HCID 7914Diisopropyl EtherHCID 86754102HCID 86754102, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To 600 mg of N,N-dimethylformamide were added 210 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 40 mg of formic acid. The solution was stirred at 120° C. for 1 hour. After 8 ml of diisopropyl ether was added and stirred, the solution was allowed to stand. The supernatant was decanted off. Then 2 ml of ethanol was added, and the solution was heated at reflux for 20 minutes and allowed to cool down. The precipitate was collected by filtration and washed with ethanol and then diisopropyl ether to give 180 mg of the title compound.

Workup

  1. stirringstirred
  2. customThe supernatant was decanted off
  3. additionThen 2 ml of ethanol was added
  4. temperaturethe solution was heated
  5. temperatureat reflux for 20 minutes
  6. temperatureto cool down
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with ethanol

Sources & evidence

ORD record
ord-5cb9508c42464895bb9e9610cbdd0ae8
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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