Triethylamine → 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

HRID 1721095Notes

Reaction equation

HRID 1721095 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([F:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:18].[C:21]([O:25][C:26]([NH:28][CH:29]1[C:33]2([CH2:35][CH2:34]2)[CH2:32][NH:31][CH2:30]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].C(N(CC)CC)C>C(#N)C>[C:21]([O:25][C:26]([NH:28][CH:29]1[C:33]2([CH2:34][CH2:35]2)[CH2:32][N:31]([C:3]2[C:2]([Cl:1])=[C:11]3[C:6]([C:7](=[O:18])[C:8]([C:15]([OH:17])=[O:16])=[CH:9][N:10]3[CH:12]3[CH2:14][CH2:13]3)=[CH:5][C:4]=2[F:19])[CH2:30]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 98359418-Chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 14930995Tert-butyl 5-azaspiro[2.4]heptan-7-ylcarbamate

Product 1

HCID 224170877-(7-Tert-butoxycarbonylamino-5-azaspiro[2,4]heptane-5-yl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 74.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

200 mg of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 150 mg of compound 11 and 70 mg of triethylamine were added to 5 ml of acetonitrile and the mixture was refluxed for 24 hours. After cooling, the solvent was removed under reduced pressure and to the residue was added water. The precipitate was collected by filtration and washed successively with water, acetonitrile, ethanol and ether and dried. The procedure gave 245 mg of 7-(7-tert-butoxycarbonylamino-5-azaspiro[2.4]heptan-5-yl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid melting at 205°-207° C.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. temperatureAfter cooling
  3. customthe solvent was removed under reduced pressure and to the residue
  4. additionwas added water
  5. filtrationThe precipitate was collected by filtration
  6. washwashed successively with water, acetonitrile, ethanol and ether
  7. customdried

Sources & evidence

ORD record
ord-b919883338b64989982d6b5267aa8ecf
Source dataset
uspto-grants-1996_04
Patent number
US05508428

Reaction notes

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