Pyridine → N-(5-(tert-Butyl)-3,3-dimethyl-2-oxo-2,3-dihydrobenzofuran-6-yl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

HRID 446148ノート

反応式

HRID 446148 の反応式
[NH2:1][C:2]1[C:13]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:12][C:5]2[C:6]([CH3:11])([CH3:10])[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.[CH3:18][CH:19]1[O:23][CH2:22][CH2:21][CH2:20]1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.[N:42]1[CH:47]=[CH:46][CH:45]=C[CH:43]=1.[C:48](=O)(OC)[O:49]C1C=C([N+]([O-])=O)C(C(C)(C)C)=CC=1Br>O>[C:14]([C:13]1[C:2]([NH:1][C:48]([C:18]2[C:19](=[O:23])[C:20]3[C:47](=[CH:46][CH:45]=[CH:22][CH:21]=3)[NH:42][CH:43]=2)=[O:49])=[CH:3][C:4]2[O:8][C:7](=[O:9])[C:6]([CH3:11])([CH3:10])[C:5]=2[CH:12]=1)([CH3:17])([CH3:16])[CH3:15]

参加物

7

反応物 5

HCID 1049PyridineHCID 73012-Methyltetrahydrofuran2 回HCID 111923Propylphosphonic anhydrideHCID 593950502-Bromo-4-tert-butyl-5-nitrophenyl methyl carbonateHCID 595441486-Amino-5-(tert-butyl)-3,3-dimethylbenzofuran-2(3H)-one

生成物 1

HCID 59544159N-(5-(tert-Butyl)-3,3-dimethyl-2-oxo-2,3-dihydrobenzofuran-6-yl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A reaction vessel was charged with compound 26 (2.926 g, 15.43 mmol), Compound 20 (4.32 g, 18.52 mmol), 2-MeTHF (35.99 mL), and subsequently 50% T3P in 2-MeTHF (13.36 g, 21.00 mmol). Pyridine (2.441 g, 2.496 mL, 30.86 mmol) was added and the suspension heated at 47.5° C.±5° C. for 18 h. After completion, the reaction was cooled to ambient temperature and 2-MeTHF (36) and water (30 ml) were added. The layers were split and the organic layer was washed with 10 wt % citric acid solution (30 ml), water (30 ml) and twice with NaHCO3 (20 ml). The organic layer was washed with brine (50 ml), separated and the solvent removed in vacuo. The crude product was dissolved in MTBE (100 ml) and hexane (200 ml) was added as an anti-solvent. A solid precipitated and the resulting slurry was stirred for two hours. The solid was collected by suction filtration and the cake was washed with hexane. The resulting product was dried in a vacuum oven at 55° C. with nitrogen bleed to give the title compound as a beige solid. 1H-NMR (400 MHZ, DMSO-d6) δ 12.96 (d J 6.4 Hz, 1H); 12.1 (s, 1H); 8.9 (d, J 6.4 Hz, 1H); 8.33 (d, J 8 Hz, 1H); 7.84-7.75 (m, 2H); 7.55-7.48 (m, 3H); 1.47 (s, 6H); 1.45 (s, 9H).

後処理

  1. temperaturethe suspension heated at 47.5° C.±5° C. for 18 h
  2. customThe layers were split
  3. washthe organic layer was washed with 10 wt % citric acid solution (30 ml), water (30 ml) and twice with NaHCO3 (20 ml)
  4. washThe organic layer was washed with brine (50 ml)
  5. customseparated
  6. customthe solvent removed in vacuo
  7. dissolutionThe crude product was dissolved in MTBE (100 ml)
  8. additionhexane (200 ml) was added as an anti-solvent
  9. customA solid precipitated
  10. filtrationThe solid was collected by suction filtration
  11. washthe cake was washed with hexane
  12. customThe resulting product was dried in a vacuum oven at 55° C. with nitrogen

出典と根拠

ORDレコード
ord-cde97024cc2d456b95dbd2e1456ab9bb
出典データセット
uspto-grants-2013_07
特許番号
US08476442B2

反応ノート

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