Dimethyl Sulfoxide → HCID 10167035, compound
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].CN1[CH2:46][CH2:45]CCC1.CS(C)=[O:49]>>[C:45]([NH: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]([CH3:26])([CH3:24])[CH3:25])=[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])(=[O:49])[CH3:46]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 (0.33 g, 1.06 mmol), (3S,4R)-4-(1-tert-butoxycarbonylaminocyclopropyl)-3-fluoro pyrrolidine (0.39 g, 1.60 mmol), 1-methylpiperidine (0.16 ml, 1.33 mmol) and dimethyl sulfoxide (13 ml) was heated at an outer temperature of 80° C. for 7 hours under a condition of 2.94×108 Pa. When analysis was carried out by a high performance liquid chromatography after completion of the reaction, formed ratio of the compound of interest 5-acetylamino-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 17%. Also, residual ratio of the starting material was 79%.
Workup
- customafter completion of the reaction
Sources & evidence
- ORD record
- ord-3646140a21614d289994a65c3819cb54
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06825353B2
Reaction notes
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