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Triethylamine → 5-Amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(4-methylamino-3,3-dimethyl-1-piperidinyl)-4-oxo-quinoline-3-carboxylic Acid

HRID 746915
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HRID 746915 반응식
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[CH:16]1[CH2:18][CH2:17]1.[CH3:23][C:24]1([CH3:32])[CH:29]([NH:30][CH3:31])[CH2:28][CH2:27][NH:26][CH2:25]1.C(N(CC)CC)C>CS(C)=O.C(#N)C>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:26]2[CH2:27][CH2:28][CH:29]([NH:30][CH3:31])[C:24]([CH3:32])([CH3:23])[CH2:25]2)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[CH:16]1[CH2:18][CH2:17]1
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 10125063HCID 10125063, 화합물HCID 105668945-Amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

생성물 1

HCID 101376665-Amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(4-methylamino-3,3-dimethyl-1-piperidinyl)-4-oxo-quinoline-3-carboxylic Acid

시약·촉매·용매 2

HCID 679
Dimethyl Sulfoxide
용매
HCID 6342Acetonitrile용매

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온도
70 °C

실험 절차

A suspension of 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-quinoline-3-carboxylic acid (0.17 g, 0.55 mmol), 3,3-dimethyl-4-methylamino piperidine (0.15 g, 1.06 mmol) and triethylamine (1 g, 10 mmol) in a mixture of dimethylsulfoxide (10 ml) and acetonitrile (10 ml) was heated at 70° C. for 18 hr. Acetonitrile was distilled off, filtered to remove suspended impurities, diluted with water (5 ml). The precipitate thus separated was filtered, washed with water, dried and purified by silicagel column chromatography. Elute from a mixture of ethyl acetate and methanol furnished the required product. Yield 0.12 g (50%), m.p. 250° C. (decomp.), C22H29FN4O4, m/z 433 (M+1), PMR (DMSO-d6): 0.9 (m, 2H), 1.0 (m, 2H), 1.0 (s, 3H), 1.1 (s, 3H), 1.8-2.0 (m, 2H), 2.6 (s, 3H), 2.8-3.2 (m, 4H), 3.5 (s, 3H), 3.6 (s, 3H), 3.65 (m, 1H), 4.0 (m, 1H), 7.2 (bs, 2H, D2O exchangeable), 8.6 (s, 1H).

후처리

  1. distillationAcetonitrile was distilled off
  2. filtrationfiltered
  3. customto remove
  4. additiondiluted with water (5 ml)
  5. customThe precipitate thus separated
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried
  9. custompurified by silicagel column chromatography
  10. washElute from a mixture of ethyl acetate and methanol

출처 및 근거

ORD 기록
ord-db339a5275994fffa49576209fe49686
출처 데이터셋
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07393957B2

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