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Triethylamine → N-[5-(Dibenz[b,f][1,4]oxazepin-10(11H)-ylcarbonyl)-2-pyridinyl]-5-fluoro-2-methylbenzamide

HRID 1457667
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반응식

HRID 1457667 반응식
[CH:1]1[C:6]2[CH2:7][NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[F:23][C:24]1[CH:25]=[CH:26][C:27]([CH3:42])=[C:28]([CH:41]=1)[C:29]([NH:31][C:32]1[N:37]=[CH:36][C:35]([C:38](Cl)=[O:39])=[CH:34][CH:33]=1)=[O:30]>ClCCl.O>[CH:1]1[C:6]2[CH2:7][N:8]([C:38]([C:35]3[CH:34]=[CH:33][C:32]([NH:31][C:29](=[O:30])[C:28]4[CH:41]=[C:24]([F:23])[CH:25]=[CH:26][C:27]=4[CH3:42])=[N:37][CH:36]=3)=[O:39])[C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=[CH:3][CH:2]=1
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 64893310,11-Dihydrodibenzo(b,f)(1,4)oxazepineHCID 155082506-(5-Fluoro-2-methylbenzoyl)aminopyridine-3-carbonyl chloride

생성물 1

HCID 9846717N-[5-(Dibenz[b,f][1,4]oxazepin-10(11H)-ylcarbonyl)-2-pyridinyl]-5-fluoro-2-methylbenzamide수율 37.4%

시약·촉매·용매 2

HCID 962Water용매
HCID 6344
Dichloromethane
용매
2회

실험 절차

To a stirred solution of 0.39 g of 10,11-dihydrodibenz[b,f][1,4]-oxazepine, 1.1 ml of triethylamine in 5 ml of dichloromethane is added 1.17 g of 6-[(5-fluoro-2-methylbenzoyl)amino]-pyridine-3-carbonyl chloride. The mixture is stirred under argon at room temperature for 16 hours, and diluted with 50 ml of dichloromethane and 20 ml of water. The organic layer is separated, washed with 20 ml each of 1M NaHCO3, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the filtrate is concentrated to dryness under vacuum. The residue is chromatographed on silica gel with ethyl acetate-hexane (1:1) as solvent to give a solid. Crystallization from ethyl acetate gives 0.335 g of off-white crystals, m.p. 180°-186° C.

후처리

  1. customThe organic layer is separated
  2. washwashed with 20 ml each of 1M NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  5. concentrationthe filtrate is concentrated to dryness under vacuum
  6. customThe residue is chromatographed on silica gel with ethyl acetate-hexane (1:1) as solvent
  7. customto give a solid
  8. customCrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-8ae733c5c82a45a0a868a63d8345f70b
출처 데이터셋
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05849735

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