Ethanol → 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-carbamoyl-1-cyclopropyl-2-methyl-propyl)-amide

HRID 446937노트

반응식

HRID 446937 반응식
[C:1]([C:3]([CH3:32])([CH3:31])[CH:4]([NH:8][C:9]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([CH:20]3[CH2:22][CH2:21]3)[N:18]=2)[N:13]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:12]=1)=[O:10])[CH:5]1[CH2:7][CH2:6]1)#[N:2].CC[OH:35]>O.[PtH]1([P](O[H]O[P]1(C)C)(C)C)[P](O)(C)C>[C:1]([C:3]([CH3:32])([CH3:31])[CH:4]([NH:8][C:9]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([CH:20]3[CH2:22][CH2:21]3)[N:18]=2)[N:13]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:29])([CH3:28])[CH3:30])[CH:12]=1)=[O:10])[CH:5]1[CH2:6][CH2:7]1)(=[O:35])[NH2:2]

참가 물질

4

반응물 2

HCID 702EthanolHCID 670092382-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-cyano-1-cyclopropyl-2,2-dimethyl-ethyl)-amide

생성물 1

HCID 673888952-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-carbamoyl-1-cyclopropyl-2-methyl-propyl)-amide수율 64%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-cyano-1-cyclopropyl-2,2-dimethyl-ethyl)-amide (163 mg, 0.36 mmol) in EtOH (9 mL) and H2O (1 mL) was added [PtH(PMe2OH)(PMe2O)2H] (15 mg, 0.036 mmol). The reaction mixture was heated at reflux for 6 h. Additional catalyst (10 mg, 0.023 mmol) was added and heating was continued overnight. The reaction mixture was cooled to room temperature and concentrated. The residue was purified by SiO2 chromatography (50% to 100% EtOAc/hexanes) to provide 108 mg (64%) of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-carbamoyl-1-cyclopropyl-2-methyl-propyl)-amide as a viscous colorless oil.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 6 h
  3. temperatureheating
  4. concentrationconcentrated
  5. customThe residue was purified by SiO2 chromatography (50% to 100% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-3904d24b61364957814d8aa9ff5fe3a3
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481541B2

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