1,2-Dichloroethane → 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (4-hydroxymethyl-tetrahydro-pyran-4-yl)-amide

HRID 2191585노트

반응식

HRID 2191585 반응식
[CH:1]1([C:4]2[N:5]=[C:6]3[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1.C(Cl)CCl.[NH2:28][C:29]1([CH2:35][OH:36])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>C(Cl)Cl.CN(C)C1C=CN=CC=1.O>[OH:36][CH2:35][C:29]1([NH:28][C:13]([C:12]2[C:6]3[C:7](=[N:8][CH:9]=[C:4]([CH:1]4[CH2:3][CH2:2]4)[N:5]=3)[N:10]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=2)=[O:15])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1

참가 물질

7

반응물 3

HCID 111,2-DichloroethaneHCID 18316484(4-Aminooxan-4-yl)methanolHCID 578296532-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

생성물 1

HCID 670020152-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (4-hydroxymethyl-tetrahydro-pyran-4-yl)-amide수율 57%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (0.20 g, 0.59 mmol) in CH2Cl2 (5 mL) was added EDC (0.14 g, 0.72 mmol), 4-(dimethylamino)pyridine (0.088 g, 0.72 mmol), and (4-aminotetrahydropyran-4-yl)-methanol (0.094 g, 0.72 mmol). The reaction mixture was stirred at room temperature overnight then diluted with H2O and extracted with CH2Cl2. The combined organics were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by SiO2 chromatography (60% EtOAc/hexanes) to obtain 0.15 g (57%) of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (4-hydroxymethyl-tetrahydro-pyran-4-yl)-amide as an oil.

후처리

  1. extractionextracted with CH2Cl2
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by SiO2 chromatography (60% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-ebb5c94234ba4b2aa08442fe6767d172
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329699B2

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