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Diisopropylethylamine → 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-oxazol-2-yl-ethyl)-amide

HRID 245920
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HRID 245920 반응식
[Br:1][C:2]1[N:3]=[C:4]2[C:10]([C:11]([OH:13])=O)=[CH:9][N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:5]2=[N:6][CH:7]=1.Cl.Cl.[O:24]1[CH:28]=[CH:27][N:26]=[C:25]1[CH:29]([NH2:31])[CH3:30].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[O:24]1[CH:28]=[CH:27][N:26]=[C:25]1[CH:29]([NH:31][C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([Br:1])[N:3]=2)[N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:9]=1)=[O:13])[CH3:30]
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참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 584385252-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acidHCID 866779151-Oxazol-2-yl-ethylamine dihydrochloride

생성물 1

HCID 86677921
2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-oxazol-2-yl-ethyl)-amide
수율 71%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A round-bottomed flask was charged with 2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (300 mg, 0.81 mmol) and 1-oxazol-2-yl-ethylamine dihydrochloride (244 mg, 1.0 mmol). DMF (4 ml) was added followed by N,N-diisopropylethylamine (0.9 ml, 5.15 mmol) and HATU (337 mg, 0.89 mmol). The reaction mixture was stirred at room temperature overnight then quenched with water and diluted with petroleum ether. The resulting suspension was filtered. The filter cake was washed with water and petroleum ether then dried under high vacuum to afford 268 mg (71%) of 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-oxazol-2-yl-ethyl)-amide as an off-white powder.

후처리

  1. customthen quenched with water
  2. additiondiluted with petroleum ether
  3. filtrationThe resulting suspension was filtered
  4. washThe filter cake was washed with water and petroleum ether
  5. customthen dried under high vacuum

출처 및 근거

ORD 기록
ord-d3bb689221e04cebbfe89b7c9db0f201
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658646B2

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