1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid → 7-(1-tert-Butoxycarbonylamino-6-azaspiro[2.5]oct-6-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

HRID 1654516Notes

Reaction equation

HRID 1654516 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:11]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:17]1([N:20]2[C:29]3[C:24](=[CH:25][C:26]([F:31])=[C:27](F)[CH:28]=3)[C:23](=[O:32])[C:22]([C:33]([OH:35])=[O:34])=[CH:21]2)[CH2:19][CH2:18]1>>[C:1]([O:5][C:6]([NH:8][CH:9]1[C:11]2([CH2:12][CH2:13][N:14]([C:27]3[CH:28]=[C:29]4[C:24]([C:23](=[O:32])[C:22]([C:33]([OH:35])=[O:34])=[CH:21][N:20]4[CH:17]4[CH2:19][CH2:18]4)=[CH:25][C:26]=3[F:31])[CH2:15][CH2:16]2)[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 15282171tert-Butyl 6-azaspiro[2.5]octan-1-ylcarbamate

Product 1

HCID 675530147-(1-tert-Butoxycarbonylamino-6-azaspiro[2.5]oct-6-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acidYield 97%

Procedure

According to the procedure of example 1A, 1-tert-butoxycarbonylamino-6-azaspiro[2.5]octane (260.0 mg, 1.15 mmol ) and 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (274 mg, 1.04 mmol) were reacted to generate the title product (472 mg, 1.00 mg, 97% yield).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-2ddc66e1863748aba46743bc164067ec
Source dataset
uspto-grants-1995_04
Patent number
US05407943

Reaction notes

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