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 1975333노트

반응식

HRID 1975333 반응식
[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]

참가 물질

5

반응물 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

생성물 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 acid수율 74.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5469eb55284040b6b1628ec9658b287b
출처 데이터셋
uspto-grants-1994_02
특허 번호
US05286723

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