5-Azaspiro[2.4]heptan-7-amine → 7-(7-Amino-5-azaspiro[2.4]heptan-5-yl)-8-chloro-1-cyclopropyl-6-fluoro-4-oxo-quinoline-3-carboxylic acid

HRID 1721089Notes

Reaction equation

HRID 1721089 reaction equation
NC1C2(CC2)CNC1.N[C@H]1C2(CC2)CNC1.C(OC([NH:24][CH:25]1[C:29]2([CH2:31][CH2:30]2)[CH2:28][N:27]([C:32]2[C:41]([Cl:42])=[C:40]3[C:35]([C:36](=[O:49])[C:37]([C:46]([OH:48])=[O:47])=[CH:38][N:39]3[CH:43]3[CH2:45][CH2:44]3)=[CH:34][C:33]=2[F:50])[CH2:26]1)=O)(C)(C)C>>[NH2:24][CH:25]1[C:29]2([CH2:30][CH2:31]2)[CH2:28][N:27]([C:32]2[C:41]([Cl:42])=[C:40]3[C:35]([C:36](=[O:49])[C:37]([C:46]([OH:48])=[O:47])=[CH:38][N:39]3[CH:43]3[CH2:45][CH2:44]3)=[CH:34][C:33]=2[F:50])[CH2:26]1

Participants

4

Reactant 3

HCID 118190595-Azaspiro[2.4]heptan-7-amineHCID 11829393(7S)-5-Azaspiro(2.4)heptan-7-amineHCID 224170877-(7-Tert-butoxycarbonylamino-5-azaspiro[2,4]heptane-5-yl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 52718237-(7-Amino-5-azaspiro[2.4]heptan-5-yl)-8-chloro-1-cyclopropyl-6-fluoro-4-oxo-quinoline-3-carboxylic acid

Procedure

For example, as for the antimicrobial activity of the two enantiomers having a 7-amino-5-azaspiro[2,4]heptane structure, one of them has more potent antimicrobial activity than the other. It has been revealed that the derivative of the 7-(S)-amino-5-azaspiro[2.4]heptane is the more potent enantiomer. This fact was confirmed by X-ray crystallographycal analysis of the one of the isomers of 7-(7-tert-butoxycarbonylamino-5-azaspiro[2.4]heptane-5-yl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid which gives the more potent isomer of 7-(7-amino-5-azaspiro[2.4]heptane-5-yl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.

Sources & evidence

ORD record
ord-97f224dc7ef84a80835464bbf446d8f2
Source dataset
uspto-grants-1996_04
Patent number
US05508428

Reaction notes

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