Sodium Carbonate → Ethyl 4-tert-Butyl-2-((2-methyl-3-(4-methyl-6-(4-(morpholine-4-carbonyl)phenyl amino)-5-oxo-4,5-dihydropyrazin-2yl)phenylamino)methyl)benzoate

HRID 1772071ノート

反応式

HRID 1772071 の反応式
Br[CH2:2][C:3]1[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:11]=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:18][C:19]1[C:20]([CH3:48])=[C:21]([C:25]2[N:26]=[C:27]([NH:33][C:34]3[CH:39]=[CH:38][C:37]([C:40]([N:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)=[O:41])=[CH:36][CH:35]=3)[C:28](=[O:32])[N:29]([CH3:31])[CH:30]=2)[CH:22]=[CH:23][CH:24]=1.C(N(C(C)C)CC)(C)C.C([O-])([O-])=O.[Na+].[Na+]>CCO>[C:14]([C:12]1[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:3]([CH2:2][NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[N:26]=[C:27]([NH:33][C:34]4[CH:35]=[CH:36][C:37]([C:40]([N:42]5[CH2:47][CH2:46][O:45][CH2:44][CH2:43]5)=[O:41])=[CH:38][CH:39]=4)[C:28](=[O:32])[N:29]([CH3:31])[CH:30]=3)[C:20]=2[CH3:48])[CH:13]=1)([CH3:17])([CH3:16])[CH3:15]

参加物

6

反応物 4

HCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 469423835-(3-Amino-2-methylphenyl)-1-methyl-3-[4-(morpholine-4-carbonyl)-phenylamino]-1H-pyrazin-2-oneHCID 66610253Ethyl 2-(bromomethyl)-4-tert-butylbenzoate

生成物 1

HCID 66610366Ethyl 4-tert-Butyl-2-((2-methyl-3-(4-methyl-6-(4-(morpholine-4-carbonyl)phenyl amino)-5-oxo-4,5-dihydropyrazin-2yl)phenylamino)methyl)benzoate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

A 48-mL sealed tube equipped with a magnetic stirring bar was charged with bromide 101c (120 mg, 0.4 mmol), aniline 101g (168 mg, 0.4 mmol), diisopropyethylamine (0.08 mL, 0.48 mmol) in EtOH (3 mL). After the mixture was stirred at 100° C. for 16 h, aqueous Na2CO3 (5 mL) was added. The aqueous phase was extracted with EtOAc (2×5 mL), and the combined organic extracts were washed with brine (5 mL), dried with Na2SO4 and concentrated. The residue was chromatographed with (gradient, 50%-100% EtOAc/hexanes) to afford 100 mg (42%) of 101h.

後処理

  1. customA 48-mL sealed tube
  2. customequipped with a magnetic stirring bar
  3. extractionThe aqueous phase was extracted with EtOAc (2×5 mL)
  4. washthe combined organic extracts were washed with brine (5 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated
  7. customThe residue was chromatographed with (gradient, 50%-100% EtOAc/hexanes)
  8. customto afford 100 mg (42%) of 101h.

出典と根拠

ORDレコード
ord-9daf8885401042fe8997172bab40218f
出典データセット
uspto-grants-2016_02
特許番号
US09249123B2

反応ノート

読み込み中…