N-Methylpiperidine → HCID 12982235, compound

HRID 2417238Notes

Reaction equation

[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([CH3:14])=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[C@@H:15]1[CH2:17][C@@H:16]1[F:18].[C:23]([O:27][C:28]([NH:30][C:31]1([C@H:34]2[CH2:38][NH:37][CH2:36][C@H:35]2[F:39])[CH2:33][CH2:32]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].CN1CCCCC1>CS(C)=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:37]2[CH2:38][C@H:34]([C:31]3([NH:30][C:28]([O:27][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:29])[CH2:32][CH2:33]3)[C@H:35]([F:39])[CH2:36]2)[C:9]([CH3:14])=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[C@@H:15]1[CH2:17][C@@H:16]1[F:18]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture consisting of 5-amino-6,7-difluoro-1-[(1R,2S)-2-fluoro-1-cyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid (45 mg, 0.144 mmol), (3S,4R)-4-(1-tert-butoxycarbonylaminocyclopropyl)-3-fluoropyrrolidine (52.8 mg, 0.216 mmol), 1-methylpiperidine (18.5 mg, 0.186 mmol) and dimethyl sulfoxide (1.8 ml) was stirred at an outer temperature of 80° C. for 7 hours. When analysis was carried out by a high performance liquid chromatography after completion of the reaction, formed ratio of the compound of interest 5-amino-7-[(3S,4R)-4-(1-tert-butoxycarbonylaminocyclopropyl)-3-fluoropyrrolidinyl]-6-fluoro-1-[(1R,2S)-2-fluoro-1-cyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid was 4%. Also, residual ratio of the starting material was 90%.

Workup

customafter completion of the reaction

Sources & evidence

ORD record: ord-d633c4fdb8a444ce9a25e72a82f8a7d8
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825353B2

Reaction notes

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