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Hydrogen Bromide → 4-(5-bromo-imidazo[1,2-a]pyrazin-8-ylamino)-2-methoxy-N-(6-methylpyridin-3-ylmethyl)benzamide

HRID 1366186
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HRID 1366186 반응식
[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5](Br)=[N:4][CH:3]=1.[NH2:12][C:13]1[CH:29]=[CH:28][C:16]([C:17]([NH:19][CH2:20][C:21]2[CH:22]=[N:23][C:24]([CH3:27])=[CH:25][CH:26]=2)=[O:18])=[C:15]([O:30][CH3:31])[CH:14]=1.Br.C([O-])(O)=O.[Na+]>CC(O)C.O>[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:12][C:13]2[CH:29]=[CH:28][C:16]([C:17]([NH:19][CH2:20][C:21]3[CH:22]=[N:23][C:24]([CH3:27])=[CH:25][CH:26]=3)=[O:18])=[C:15]([O:30][CH3:31])[CH:14]=2)=[N:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 534859495,8-Dibromoimidazo[1,2-a]pyrazineHCID 575900544-amino-2-methoxy-N-[(6-methylpyridin-3-yl)methyl]benzamide

생성물 1

HCID 590230284-(5-bromo-imidazo[1,2-a]pyrazin-8-ylamino)-2-methoxy-N-(6-methylpyridin-3-ylmethyl)benzamide수율 41.7%

시약·촉매·용매 2

HCID 962Water용매
HCID 3776Isopropanol용매

실험 절차

5,8-dibromoimidazo[1,2-a]pyrazine (285 mg, 1.03 mmol) and 4-amino-2-methoxy-N-[(6-methylpyridin-3-yl)methyl]benzamide (280 mg, 1.03 mmol) are stirred in iPrOH (5 mL) and HBr (48% aq., 380 μL) is added. The mixture is heated at reflux for 24 hours. The cooled suspension is poured into NaHCO3 (sat. aq., 25 mL) and water (25 mL) and extracted with CDCl3 (3×40 mL). The extracts are dried over MgSO4 and evaporated. The residue is purified by column chromatography, eluting with 10% -20% DCM/MeOH to afford the title compound as a pale yellow solid (200 mg, 0.43 mmol).

후처리

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 24 hours
  3. extractionextracted with CDCl3 (3×40 mL)
  4. dry with materialThe extracts are dried over MgSO4
  5. customevaporated
  6. customThe residue is purified by column chromatography
  7. washeluting with 10% -20% DCM/MeOH

출처 및 근거

ORD 기록
ord-7d265d1e5f4f417cb0db23dd809ea290
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07893058B2

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