Isopropyl iodide → (1-isopropyl-1H-benzo[d]imidazol-2-yl) (4-(3-morpholinopyrazin-2-yloxy)phenyl)methanone

HRID 887387ノート

反応式

HRID 887387 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[N:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11].C(=O)([O-])[O-].[K+].[K+].I[CH:38]([CH3:40])[CH3:39]>CN(C=O)C>[CH:38]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:13]=[CH:14][C:15]([O:18][C:19]2[C:24]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[N:23][CH:22]=[CH:21][N:20]=2)=[CH:16][CH:17]=1)=[O:11])([CH3:40])[CH3:39]

参加物

5

反応物 3

HCID 6362Isopropyl iodide2 回HCID 11430Potassium CarbonateHCID 462079381h-Benzimidazol-2-Yl(4-{[3-(Morpholin-4-Yl)pyrazin-2-Yl]oxy}phenyl)methanone

生成物 1

HCID 46207942(1-isopropyl-1H-benzo[d]imidazol-2-yl) (4-(3-morpholinopyrazin-2-yloxy)phenyl)methanone

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of (1H-benzo[d]imidazol-2-yl)(4-(3-morpholinopyrazin-2-yloxy)-phenyl)methanone (115 mg, 286 μmol), potassium carbonate (79.2 mg, 573 μmol) and 2-iodopropane (97.4 mg, 573 μmol) in DMF (2 mL) was stirred overnight. Additional isopropyl iodide was added until the starting material was consumed. The mixture was diluted with water and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate and the combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by Biotage™, 10-30% acetone/hexanes gradient, to give (1-isopropyl-1H-benzo[d]imidazol-2-yl) (4-(3-morpholinopyrazin-2-yloxy)phenyl)methanone. MS (ESI, pos. ion) m/z: 444.1 (M+1). IC50 (uM) ++++.

後処理

  1. customwas consumed
  2. additionThe mixture was diluted with water and ethyl acetate
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washthe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by Biotage™, 10-30% acetone/hexanes gradient

出典と根拠

ORDレコード
ord-5a0cd9af8f4f49b49524f6cee31856b3
出典データセット
uspto-grants-2012_08
特許番号
US08247418B2

反応ノート

読み込み中…