Triethylamine → 2-cyclopropyl-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-methyl-2-oxo-piperidin-3-yl)-amide

HRID 446945노트

반응식

HRID 446945 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.[NH2:24][C@@H:25]1[CH2:30][CH2:29][CH2:28][N:27]([CH3:31])[C:26]1=[O:32].C(N(CC)CC)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH3:31][N:27]1[CH2:28][CH2:29][CH2:30][C@@H:25]([NH:24][C:13]([C:12]2[C:6]3[C:7](=[N:8][CH:9]=[C:4]([CH:1]4[CH2:2][CH2:3]4)[N:5]=3)[N:10]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:21])([CH3:22])[CH3:23])[CH:11]=2)=[O:15])[C:26]1=[O:32]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 57516592(R)-3-Amino-1-methylpiperidin-2-oneHCID 578296532-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

생성물 1

HCID 673880382-cyclopropyl-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-methyl-2-oxo-piperidin-3-yl)-amide수율 74.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (150 mg, 0.45 mmol) and (R)-3-amino-1-methyl-piperidin-2-one (115 mg, 0.90 mmol) in DMF (2.4 mL) at room temperature was added triethylamine (0.19 mL, 1.35 mmol) and PyBOP (257 mg, 0.50 mmol). The reaction mixture was stirred overnight then diluted with EtOAc (30 mL) and washed with water (4×30 mL). The combined organic extracts were dried (Na2SO4) and evaporated under vacuum. The crude residue was purified by SiO2 column chromatography (11 g, CH2Cl2/MeOH/NH4OH, 100:0:0 to 94:5.7:0.3) to give 149 mg (74%) of 2-cyclopropyl-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-methyl-2-oxo-piperidin-3-yl)-amide as a colorless viscous oil.

후처리

  1. washwashed with water (4×30 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. customevaporated under vacuum
  4. customThe crude residue was purified by SiO2 column chromatography (11 g, CH2Cl2/MeOH/NH4OH, 100:0:0 to 94:5.7:0.3)

출처 및 근거

ORD 기록
ord-3dea49ab27f145379f38a1fa87a9485c
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481541B2

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