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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 1924962
ノート
印刷プレビュー

反応式

HRID 1924962 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 3776Isopropanol溶媒

実験手順

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 CHCl3 (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).

後処理

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 24 hours
  3. extractionextracted with CHCl3 (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

出典と根拠

ORDレコード
ord-633ff21f22354fd5b2401811a5e51949
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08178530B2

反応ノート

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