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 1772071노트

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HRID 1772071 반응식
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]

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
100 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-9daf8885401042fe8997172bab40218f
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249123B2

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