Pyridine → N-(2-(tert-Butyl)-5-hydroxy-4-(1-hydroxy-2-methylpropan-2-yl)phenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

HRID 76782ノート

反応式

HRID 76782 の反応式
C(=O)([O-])OC[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][C:5]=1[C:15]([CH3:23])([CH3:22])[CH2:16][O:17]C(OC)=O.[O:26]=[C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=[C:28]1[C:37](O)=[O:38].N1C=CC=CC=1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)[O:50]1)CC.C[O-].[Na+]>CC1OCCC1.O>[C:11]([C:7]1[CH:6]=[C:5]([C:15]([CH3:22])([CH3:23])[CH2:16][OH:17])[C:4]([OH:50])=[CH:9][C:8]=1[NH:10][C:37]([C:28]1[C:27](=[O:26])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)=[O:38])([CH3:12])([CH3:13])[CH3:14]

参加物

8

反応物 5

HCID 1049PyridineHCID 111923Propylphosphonic anhydrideHCID 2208754-Quinolone-3-carboxylic acidHCID 10942334Sodium MethoxideHCID 86663357[5-Amino-4-tert-butyl-2-(2-methoxycarbonyloxy-1,1-dimethyl-ethyl)phenyl]methyl carbonate

生成物 1

HCID 46897962N-(2-(tert-Butyl)-5-hydroxy-4-(1-hydroxy-2-methylpropan-2-yl)phenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 73012-Methyltetrahydrofuran溶媒2 回

反応条件

温度
50 °C

実験手順

To a mixture of [5-amino-4-tert-butyl-2-(2-methoxycarbonyloxy-1,1-dimethyl-ethyl)phenyl]methyl carbonate (103 mg, 0.29 mmol), 4-oxo-1,4-dihydroquinoline-3-carboxylic acid (50 mg, 0.26 mmol), and pyridine (42 mg, 0.53 mmol) in 2-MeTHF (3.0 mL) was charged T3P as a 50 wt % solution in 2-MeTHF (286 mg, 0.45 mmol). The mixture was heated to 50° C. for 18 h. After cooling to ambient temperature, the mixture was diluted with water. The organic phase was separated and again washed with water. Sodium methoxide (39 mg, 0.72 mmol) was charged to the organic phase and the solution stirred for 2 hours. The reaction was quenched with 1N HCl, and after separating the phases, the organic phase was washed with 0.1N HCl. The organic phase was than dried in vacuo to yield Compound 27 as a solid. The 1H-NMR spectrum was consistent with that reported above.

後処理

  1. temperatureAfter cooling to ambient temperature
  2. customThe organic phase was separated
  3. washagain washed with water
  4. customThe reaction was quenched with 1N HCl
  5. customafter separating the phases
  6. washthe organic phase was washed with 0.1N HCl
  7. customthan dried in vacuo

出典と根拠

ORDレコード
ord-2f553a502e6240029474c15b0f14c552
出典データセット
uspto-grants-2014_09
特許番号
US08835639B2

反応ノート

読み込み中…