N-Hydroxy-3-pyridinecarboximidoyl chloride → 7-[cis-3-(3-Pyridyl)-3a,4,6,6a-tetrahydropyrrolo[3,4-d]isoxazol-5-yl]-1-cyclopropyl-8-methoxy-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 600736Notes

Reaction equation

HRID 600736 reaction equation
N1C=CC=CC=1[C:7]1[C@@H:11]2[CH2:12][N:13]([C:15]3[C:24]([O:25][CH3:26])=[C:23]4[C:18]([C:19](=[O:33])[C:20]([C:30]([OH:32])=[O:31])=[CH:21][N:22]4[CH:27]4[CH2:29][CH2:28]4)=[CH:17][C:16]=3[F:34])[CH2:14][C@@H:10]2[O:9][N:8]=1.ON=C(Cl)[C:38]1[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=1>>[N:40]1[CH:41]=[CH:42][CH:43]=[C:38]([C:7]2[C@@H:11]3[CH2:12][N:13]([C:15]4[C:24]([O:25][CH3:26])=[C:23]5[C:18]([C:19](=[O:33])[C:20]([C:30]([OH:32])=[O:31])=[CH:21][N:22]5[CH:27]5[CH2:29][CH2:28]5)=[CH:17][C:16]=4[F:34])[CH2:14][C@@H:10]3[O:9][N:8]=2)[CH:39]=1

Participants

3

Reactant 2

HCID 53404818N-Hydroxy-3-pyridinecarboximidoyl chlorideHCID 689744027-[cis-3-(2-Pyridyl)-3a,4,6,6a-tetrahydropyrrolo[3,4-d]isoxazol-5-yl]-1-cyclopropyl-8-methoxy-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 689725617-[cis-3-(3-Pyridyl)-3a,4,6,6a-tetrahydropyrrolo[3,4-d]isoxazol-5-yl]-1-cyclopropyl-8-methoxy-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Procedure

The title compound was prepared in an analogous manner to acid 122, but using chloro oxime 2f. Acid 123 was isolated.

Sources & evidence

ORD record
ord-941e00a08d7a46b1992140c58873aa6f
Source dataset
uspto-grants-2011_03
Patent number
US07902227B2

Reaction notes

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