Dimethylformamide → Diisopropyl Ether

HRID 1415942Notes

Reaction equation

CN(C)C=O.[NH2:6][C:7]1[CH:8]=[C:9]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([F:26])=[C:22](Cl)[N:23]=3)[C:18](=[O:27])[C:17]([C:28]([OH:30])=[O:29])=[CH:16]2)[C:10]([F:14])=[CH:11][C:12]=1[F:13].[OH:31][CH:32]1[CH2:36][CH2:35][NH:34][CH2:33]1.[CH:37]([O:40][CH:41]([CH3:43])[CH3:42])([CH3:39])[CH3:38]>C(N(CC)CC)C>[CH:37]([O:40][CH:41]([CH3:43])[CH3:42])([CH3:39])[CH3:38].[NH2:6][C:7]1[CH:8]=[C:9]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([F:26])=[C:22]([N:34]4[CH2:35][CH2:36][CH:32]([OH:31])[CH2:33]4)[N:23]=3)[C:18](=[O:27])[C:17]([C:28]([OH:30])=[O:29])=[CH:16]2)[C:10]([F:14])=[CH:11][C:12]=1[F:13]

Participants

Conditions

Temperature: 70 °C

Procedure

To 550 mg of N,N-dimethylformamide were added 150 mg of 1-(3-amino-4,6-difluorophenyl)-7-chloro-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid, 100 mg of 3-hydroxypyrrolidine, and 100 mg of triethylamine. The solution was stirred at 70° C. for 30 minutes. The reaction solution was combined with 8 ml of diisopropyl ether, stirred, and allowed to stand. The supernatant was removed by decantation. To the remainder was added 2 ml of ethanol. The precipitate was collected by filtration and washed with ethanol and then with diisopropyl ether to give 156 mg of the title compound.

Workup

stirringstirred
customThe supernatant was removed by decantation
additionTo the remainder was added 2 ml of ethanol
filtrationThe precipitate was collected by filtration
washwashed with ethanol

Sources & evidence

ORD record: ord-6566febd02394987a82f9a7e0a2de1a9
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05910498

Reaction notes

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