2-(1,3-Dioxoisoindolin-2-yl)ethyl trifluoromethanesulfonate → 2-(3-Chloroanilino)-4-[1-(2-phthalimidoethyl)imidazol-5-yl]pyrimidine

HRID 1064307ノート

反応式

HRID 1064307 の反応式
O([CH2:9][CH2:10][N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])S(C(F)(F)F)(=O)=O.[Cl:22][C:23]1[CH:24]=[C:25]([CH:57]=[CH:58][CH:59]=1)[NH:26][C:27]1[N:32]=[C:31]([C:33]2[N:34]=[CH:35][N:36](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:37]=2)[CH:30]=[CH:29][N:28]=1>C(Cl)Cl>[Cl:22][C:23]1[CH:24]=[C:25]([CH:57]=[CH:58][CH:59]=1)[NH:26][C:27]1[N:32]=[C:31]([C:33]2[N:34]([CH2:9][CH2:10][N:11]3[C:15](=[O:16])[C:14]4=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]4[C:12]3=[O:21])[CH:35]=[N:36][CH:37]=2)[CH:30]=[CH:29][N:28]=1

参加物

4

反応物 2

HCID 118094652-(1,3-Dioxoisoindolin-2-yl)ethyl trifluoromethanesulfonateHCID 222735042-(3-Chloroanilino)-4-(1-triphenylmethylimidazol-4-yl)pyrimidine

生成物 1

HCID 222735062-(3-Chloroanilino)-4-[1-(2-phthalimidoethyl)imidazol-5-yl]pyrimidine収率 40%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-Phthalimidoethyl triflate (660 mg, 2.04 mmol) was added to solution of the 2-(3-chloroanilino)-4-(1-triphenylmethylimidazol-4-yl)pyrimidine Method 2; 1.00 g, 1.95 mmol) in DCM (5 ml) and the reaction mixture stirred for 4 hours. The solvent was removed by evaporation and MeOH (6 ml) and 2M hydrochloric acid (1.5 ml) was added to the residue. The mixture was stirred for 5 minutes, the volatiles were removed by evaporation and the residue partitioned between EtOAc and saturated aqueous sodium hydrogen carbonate solution. The resulting precipitate was collected by filtration, washed with water and EtOAc and dried to give the title compound 350 mg, (40%) as a solid. NMR: 3.81-3.96 (m, 2H), 4.77-4.92 (m, 2H), 6.98 (d, 1H), 7.06 (d, 1H), 7.31 (t, 1H), 7.37 (d, 1H), 7.63-7.80 (m, 6H), 7.92 (s, 1H), 8.27 (d, 1H), 9.50 (s, 1H); m/z: 443.

後処理

  1. customThe solvent was removed by evaporation and MeOH (6 ml) and 2M hydrochloric acid (1.5 ml)
  2. additionwas added to the residue
  3. customthe volatiles were removed by evaporation
  4. customthe residue partitioned between EtOAc and saturated aqueous sodium hydrogen carbonate solution
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water and EtOAc
  7. customdried

出典と根拠

ORDレコード
ord-07c2d75e86964e0281dee757f53057c8
出典データセット
uspto-grants-2005_11
特許番号
US06969714B2

反応ノート

読み込み中…