Hydrogen Bromide → 4-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-2-hydroxy-N-[(6-methyl-pyridin-3-yl)methyl]benzamide

HRID 605993ノート

反応式

HRID 605993 の反応式
[Br:1][C:2]1[N:7]2[N: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]C)[CH:14]=1.Br.C([O-])(O)=O.[Na+]>CC(O)C.O>[Br:1][C:2]1[N:7]2[N: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]([OH:30])[CH:14]=2)=[N:4][CH:3]=1

参加物

7

反応物 4

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 497580225,8-Dibromo-(1,2,4)triazolo(1,5-a)pyrazineHCID 575900544-amino-2-methoxy-N-[(6-methylpyridin-3-yl)methyl]benzamide

生成物 1

HCID 866196654-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-2-hydroxy-N-[(6-methyl-pyridin-3-yl)methyl]benzamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3776Isopropanol溶媒

実験手順

5,8-Dibromo-[1,2,4]triazolo[1,5-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 (4×30 mL). The extracts are dried over MgSO4 and evaporated. The residue is purified by column chromatography, eluting with 10% CH2Cl2/MeOH. The product-containing fractions are evaporated and the residue is triturated with MeOH to afford the title compound as a brown solid.

後処理

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 24 hours
  3. extractionextracted with CHCl3 (4×30 mL)
  4. dry with materialThe extracts are dried over MgSO4
  5. customevaporated
  6. customThe residue is purified by column chromatography
  7. washeluting with 10% CH2Cl2/MeOH
  8. customThe product-containing fractions are evaporated
  9. customthe residue is triturated with MeOH

出典と根拠

ORDレコード
ord-ca39508f3f434463b7331147ab467d75
出典データセット
uspto-grants-2011_03
特許番号
US07915256B2

反応ノート

読み込み中…