1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-Amino-7-(3-amino-3-methyl1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro4-oxoquinoline-3-carboxylic acid

HRID 477020노트

반응식

HRID 477020 반응식
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.[NH2:22][C:23]1([CH3:28])[CH2:27][CH2:26][NH:25][CH2:24]1.C1CCN2C(=NCCC2)CC1>C(#N)C>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:25]2[CH2:26][CH2:27][C:23]([NH2:22])([CH3:28])[CH2:24]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 155958533-Methylpyrrolidin-3-amine

생성물 1

HCID 157293795-Amino-7-(3-amino-3-methyl1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro4-oxoquinoline-3-carboxylic acid수율 60.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.5 g), 3-amino-3-methylpyrrolidine (0.76 g), DBU (0.77 g), and acetonitrile (30 ml) was refluxed for 7 hours. The precipitated crystals were collected by filtration after cooling, and washed with acetonitrile. The crystals were suspended in water (50 ml) and dissolved by addition of a 10% aqueous solution of acetic acid. The solution was treated with activated carbon, and adjusted to pH 7-8 with 10% aqueous ammonia. The precipitated crystals were collected by filtration, washed with water and then with ethanol, and dried to give 5-amino-7-(3-amino-3-methyl1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro4-oxoquinoline-3-carboxylic acid (1.15 g), m.p. 271°-273° C. (decomp.).

후처리

  1. temperaturewas refluxed for 7 hours
  2. filtrationThe precipitated crystals were collected by filtration
  3. temperatureafter cooling
  4. washwashed with acetonitrile
  5. dissolutiondissolved by addition of a 10% aqueous solution of acetic acid
  6. additionThe solution was treated with activated carbon
  7. filtrationThe precipitated crystals were collected by filtration
  8. washwashed with water
  9. dry with materialwith ethanol, and dried

출처 및 근거

ORD 기록
ord-2acbf4ed0ca046c9971338733affc3b8
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04886810

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