Dimethylformamide → Vilazodone methyl ester

HRID 1056551ノート

反応式

HRID 1056551 の反応式
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]3[O:14][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][C:11]=3[CH:19]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C1(C)C=CC(S(O[CH2:30][CH2:31][CH2:32][CH2:33][C:34]2[C:42]3[C:37](=[CH:38][CH:39]=[C:40]([C:43]#[N:44])[CH:41]=3)[NH:36][CH:35]=2)(=O)=O)=CC=1.C(N(CC)CC)C.CN(C)C=O>O>[C:43]([C:40]1[CH:41]=[C:42]2[C:37](=[CH:38][CH:39]=1)[NH:36][CH:35]=[C:34]2[CH2:33][CH2:32][CH2:31][CH2:30][N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][C:11]=3[CH:19]=2)[CH2:6][CH2:5]1)#[N:44]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 569522673-[4-(p-Toluenesulfonyloxy)butyl]-1H-indole-5-carbonitrileHCID 77231352Methyl 5-(piperazin-1-yl)benzofuran-2-carboxylate

生成物 1

HCID 19438830Vilazodone methyl ester収率 121.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
79.5 °C

実験手順

Methyl 5-(1-piperazinyl)benzofuran-2-carboxylate (5 g), 3-[4-(p-toluenesulfonyloxy)butyl]-1H-indole-5-carbonitrile (6.3 g) and triethylamine (7 ml) were added to dimethylformamide (6.3 ml) and the resulting mixture was heated to 77-82° C., followed by stirring for 45 minutes at the same temperature. Water (30 ml) was added to the reaction mass and then stirred for 5 minutes at 25-30° C. The separated aqueous layer was extracted two times with toluene (2×250 ml). The resulting organic layers were combined and then washed two times with water (2×250 ml) and then distilled off the solvent under vacuum to produce 9.5 g of the titled compound as a residue. Methanol (47.5 ml) was added to the residue at 25-30° C. and then stirred for 30 minutes at the same temperature. The separated solid was filtered, washed with chilled methanol (10 ml) and then dried the material at 70-75° C. to produce 6 g of Methyl 5-[4-[4-(5-cyanoindol-3-yl)butyl]piperazin-1-yl]benzofuran-2-carboxylate (Purity by HPLC: 99%; Yield: 76.9%).

後処理

  1. stirringstirred for 5 minutes at 25-30° C
  2. extractionThe separated aqueous layer was extracted two times with toluene (2×250 ml)
  3. washwashed two times with water (2×250 ml)
  4. distillationdistilled off the solvent under vacuum

出典と根拠

ORDレコード
ord-15eef5d7ac4e4f7097cce45b5c6b3ef8
出典データセット
uspto-grants-2016_07
特許番号
US09399630B2

反応ノート

読み込み中…