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Ethylenediamine → 2-(6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-oxazol-2-yl-ethyl)-amide

HRID 245922
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HRID 245922 반응식
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C@H:6]([NH:8][C:9]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([C:20]3[N:21]=[CH:22][N:23]4[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=34)[N:18]=2)[N:13](COCC[Si](C)(C)C)[CH:12]=1)=[O:10])[CH3:7].FC(F)(F)C(O)=O.C(N)CN>ClCCl>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C@H:6]([NH:8][C:9]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([C:20]3[N:21]=[CH:22][N:23]4[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=34)[N:18]=2)[NH:13][CH:12]=1)=[O:10])[CH3:7]
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참가 물질

5

반응물 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 712881952-(6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-oxazol-2-yl-ethyl)-amide

생성물 1

HCID 712881782-(6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-oxazol-2-yl-ethyl)-amide수율 94.7%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

In a round-bottomed flask, 2-(6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-oxazol-2-yl-ethyl)-amide (107 mg, 0.205 mmol) was dissolved in dichloromethane (1.1 ml) and trifluoroacetic acid (0.64 ml, 8.3 mmol) was added. The reaction mixture was stirred at room temperature for 2 h then concentrated. The residue was dissolved in dichloromethane (1.1 ml) and ethylenediamine (0.84 ml, 12.4 mmol) was added. The yellow reaction mixture was stirred at room temperature for 1 h then quenched with water and diluted with ethyl acetate. The resultant suspension was filtered, washed with hot water and ethyl acetate and dried under high vacuum to provide 76 mg (90%) of 2-(6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-oxazol-2-yl-ethyl)-amide as a yellow powder. MS: (M+Na)+=414; 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 12.76 (br. s., 1H), 9.12 (s, 1H), 8.70 (dd, J=4.7, 2.1 Hz, 1H), 8.60 (d, J=8.7 Hz, 1H), 8.54 (s, 1H), 8.36-8.46 (m, 2H), 8.11 (s, 1H), 7.25 (s, 1H), 7.04 (ddd, J=9.9, 7.8, 1.9 Hz, 1H), 5.45-5.60 (m, 1H), 1.65 (d, J=6.8 Hz, 3H).

후처리

  1. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in dichloromethane (1.1 ml)
  3. stirringThe yellow reaction mixture was stirred at room temperature for 1 h
  4. customthen quenched with water
  5. additiondiluted with ethyl acetate
  6. filtrationThe resultant suspension was filtered
  7. washwashed with hot water and ethyl acetate
  8. customdried under high vacuum

출처 및 근거

ORD 기록
ord-f6abe8072bee4553834125dd1210ce72
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658646B2

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