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Ethylenediamine → HCID 71288437, 화합물

HRID 246207
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HRID 246207 반응식
[OH:1][CH2:2][C@H:3]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[C:25]4[C:20](=[CH:21][C:22]([Cl:26])=[CH:23][CH:24]=4)[N:19]([CH3:27])[N:18]=3)[N:15]=2)[N:10](COCC[Si](C)(C)C)[CH:9]=1)=[O:7])[CH3:4].C(Cl)Cl.C(N)CN>C(O)(C(F)(F)F)=O>[OH:1][CH2:2][C@H:3]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[C:25]4[C:20](=[CH:21][C:22]([Cl:26])=[CH:23][CH:24]=4)[N:19]([CH3:27])[N:18]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])[CH3:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 3301EthylenediamineHCID 6344DichloromethaneHCID 712860912-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-2-hydroxy-1-methyl-ethyl)-amide

생성물 1

HCID 71288437HCID 71288437, 화합물수율 57%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid
용매

실험 절차

2-(6-Chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-2-hydroxy-1-methyl-ethyl)-amide (35 mg, 0.068 mol) was dissolved in a 4:6 solution of TFA:DCM (10 mL). After stirring at room temperature overnight, the volatiles were removed under reduced pressure. The crude material was then dissolved in dichloromethane and treated with ethylenediamine (41 mg, 0.68 mmol). After stirring at room temperature overnight, the precipitate was collected by filtration to afford 15 mg (57%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-2-hydroxy-1-methyl-ethyl)-amide as a yellow solid. MS: (M+H)+=385; 1H NMR (300 MHz, DMSO-d6) δ ppm 8.97 (d, J=2.64 Hz, 1H) 8.66 (d, J=8.69 Hz, 1H) 8.36 (s, 1H) 8.15 (d, J=7.93 Hz, 1H) 7.92 (s, 1H) 7.26 (d, J=8.31 Hz, 1H) 3.96-4.39 (m, 3H) 3.31-3.68 (m, 1H) 1.25 (d, J=6.80 Hz, 3H).

후처리

  1. customthe volatiles were removed under reduced pressure
  2. dissolutionThe crude material was then dissolved in dichloromethane
  3. stirringAfter stirring at room temperature overnight
  4. filtrationthe precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-b088a429c3f247e486eeeedc0a0dad9c
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658646B2

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