Sodium Thiosulfate → 5-[1-tert-Butyl-2-(2-1,2,4-triazol-1-yl-phenyl)-1H-benzimidazol-5-yl]-4-methoxy-pyrimidin-2-ylamine

HRID 1966740ノート

反応式

HRID 1966740 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10]2[CH:11]=[C:12]([NH2:21])[C:13]([NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:14][CH:15]=2)=[CH:4][N:3]=1.[N:22]1([C:27]2[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=2[CH:29]=O)[CH:26]=[N:25][CH:24]=[N:23]1.OOS([O-])=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C.O.CCOC(C)=O>[C:17]([N:16]1[C:13]2[CH:14]=[CH:15][C:10]([C:5]3[C:6]([O:8][CH3:9])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=3)=[CH:11][C:12]=2[N:21]=[C:29]1[C:28]1[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=1[N:22]1[CH:26]=[N:25][CH:24]=[N:23]1)([CH3:18])([CH3:20])[CH3:19]

参加物

8

反応物 4

HCID 24477Sodium ThiosulfateHCID 35364462-(1H-1,2,4-Triazol-1-yl)benzaldehydeHCID 23707502Potassium hydroxy sulfiteHCID 585420094-(2-amino-4-methoxy-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine

生成物 1

HCID 585419935-[1-tert-Butyl-2-(2-1,2,4-triazol-1-yl-phenyl)-1H-benzimidazol-5-yl]-4-methoxy-pyrimidin-2-ylamine収率 37%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a round bottom flask is added 4-(2-amino-4-methoxy-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (118 mg, 0.411 mmol) in DMF (4 mL) and water (1 mL), followed by the addition of 2-1,2,4-triazol-1-yl-benzaldehyde (78 mg, 0.45 mmol) and oxone (51 mg, 0.443 mmol). The reaction mixture is stirred at room temperature for 4 hours. Sat. sodium thiosulfate (10 mL) is added. The reaction mixture is diluted with EtOAc. The organic layer is separated, washed with water then brine, dried with Na2SO4, filtered and concentrated. The residue is loaded into a silica gel column. The column is eluted with 0-4% 7M NH3 in MeOH/CH2Cl2. The product fractions are collected and concentrated to afford the title compound (67 mg, 37%) as a light brown solid. LCMS (ESMS): m/z 441.73 (M++1)

後処理

  1. customThe organic layer is separated
  2. washwashed with water
  3. dry with materialbrine, dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe column is eluted with 0-4% 7M NH3 in MeOH/CH2Cl2
  7. customThe product fractions are collected
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-c4355cb4f04a4de8bc587ca5886a25a9
出典データセット
uspto-grants-2013_04
特許番号
US08420655B2

反応ノート

読み込み中…