Dichloromethane → 3-cyclopropyl-3-(4-(3-iodo-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile

HRID 1852978ノート

反応式

HRID 1852978 の反応式
[CH:1]1([CH:4]([N:8]2[CH:12]=[C:11]([C:13]3[N:18]4[CH:19]=[CH:20][N:21]=[C:17]4[CH:16]=[C:15]([C:22]4[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=4)[N:14]=3)[CH:10]=[N:9]2)[CH2:5][C:6]#[N:7])[CH2:3][CH2:2]1.[I:28]N1C(=O)CCC1=O.C(Cl)Cl>CCOC(C)=O>[CH:1]1([CH:4]([N:8]2[CH:12]=[C:11]([C:13]3[N:18]4[C:19]([I:28])=[CH:20][N:21]=[C:17]4[CH:16]=[C:15]([C:22]4[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=4)[N:14]=3)[CH:10]=[N:9]2)[CH2:5][C:6]#[N:7])[CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 120273N-IodosuccinimideHCID 534974533-cyclopropyl-3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile

生成物 1

HCID 866853053-cyclopropyl-3-(4-(3-iodo-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile収率 75.7%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

3-cyclopropyl-3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile (Example 2; 84.6 mg, 0.236 mmol) and 1-iodopyrrolidine-2,5-dione (79.7 mg, 0.354 mmol) were suspended in DCM (2.36 mL, 0.236 mmol) and stirred at ambient temperature for 15 hours. The reaction mixture was diluted in EtOAc and washed with saturated sodium bicarbonate and brine. The organic layer was dried with MgSO4, filtered and concentrated in vacuo. Purification of the resulting crude material by silica chromatography using 0-5% MeOH/EtOAc gradient afforded 3-cyclopropyl-3-(4-(3-iodo-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile (86.5 mg, 75.7% yield). MS (apci) m/z=485.2 (M+H).

後処理

  1. washwashed with saturated sodium bicarbonate and brine
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the resulting crude material by silica chromatography

出典と根拠

ORDレコード
ord-7196752598b84a2abf7c664b8539365f
出典データセット
uspto-grants-2015_02
特許番号
US08962596B2

反応ノート

読み込み中…