1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 7-(1-tert-Butoxycarbonylamino-6-azaspiro[2.5]oct-6-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

HRID 1654519Notes

Reaction equation

HRID 1654519 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:32])=[C:27](F)[C:28]=3[F:30])[C:23](=[O:33])[C:22]([C:34]([OH:36])=[O:35])=[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[C:28]([F:30])=[C:29]4[C:24]([C:23](=[O:33])[C:22]([C:34]([OH:36])=[O:35])=[CH:21][N:20]4[CH:17]4[CH2:19][CH2:18]4)=[CH:25][C:26]=3[F:32])[CH2:15][CH2:16]2)[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 15282171tert-Butyl 6-azaspiro[2.5]octan-1-ylcarbamate

Product 1

HCID 703471427-(1-tert-Butoxycarbonylamino-6-azaspiro[2.5]oct-6-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acidYield 99.9%

Procedure

According to the procedure of example 1A, 1-tert-butoxycarbonylamino-6-azaspiro[2.5]octane (181.2 mg, 0.80 mmol) and 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (239.8 mg, 0.72 mmol) were reacted to generate the title product (352.2 mg, crude).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-7f70ae2e65b8440f9458a53b9f608def
Source dataset
uspto-grants-1995_04
Patent number
US05407943

Reaction notes

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