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

HRID 1457667
ノート
印刷プレビュー

反応式

HRID 1457667 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6344
Dichloromethane
溶媒
2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8ae733c5c82a45a0a868a63d8345f70b
出典データセット
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05849735

反応ノート

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