Pyridine → Sufugolix

HRID 23255ノート

反応式

HRID 23255 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:33][C:11]3[N:12]([CH2:24][C:25]4[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=4[F:32])[C:13](=[O:23])[N:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:15](=[O:16])[C:10]=3[C:9]=2[CH2:34][N:35]([CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH3:36])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl.[CH3:51][O:52][NH2:53].C(N(CC)CC)C.C[C:62](N(C)C)=[O:63]>O>[CH2:37]([N:35]([CH2:34][C:9]1[C:10]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:13](=[O:23])[N:12]([CH2:24][C:25]3[C:26]([F:32])=[CH:27][CH:28]=[CH:29][C:30]=3[F:31])[C:11]=2[S:33][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:62]([NH:53][O:52][CH3:51])=[O:63])=[CH:7][CH:6]=1)[CH3:36])[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

参加物

7

反応物 5

HCID 1049PyridineHCID 8471TriethylamineHCID 31374DimethylacetamideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 109190521-(2,6-difluorobenzyl)-6-(4-aminophenyl)-5-((benzyl(methyl)amino)methyl)-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

生成物 1

HCID 3038517Sufugolix収率 98.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

6-(4-aminophenyl)-5-(N-benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-3-phenylthieno[2,3-d]pyrimidine-2,4(1H, 3H)-dione (0.50 g, 0.84 mmol) was dissolved in dimethyl acetamide (2 ml), pyridine (82 μl, 1.01 mmol) was added thereto, and the mixture was stirred. Phenyl chloroformate (phenyl chlorocarbonate)(126 μl, 1.01 mmol) was added thereto dropwise under ice-cooling, and the mixture was stirred at room temperature for 2 hours. O-methylhydroxylamine hydrochloride (77.2 mg, 92.4 μmol) and triethylamine (336 μl, 2.77 mmol) were added thereto, and the mixture was stirred at 50° C. for 12 hours. Water (30 ml) was added thereto, and the mixture was vigorously stirred. The crystals were filtered, and dried under vacuum at 40° C. to give white crystals of 5-(N-benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-6-[4-(3-methoxyureido)phenyl]-3-phenylthieno[2,3-d]pyrimidine-2,4(1H, 3H)-dione (0.55 g, 98.2%).

後処理

  1. temperaturedropwise under ice-cooling
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. stirringthe mixture was stirred at 50° C. for 12 hours
  4. stirringthe mixture was vigorously stirred
  5. filtrationThe crystals were filtered
  6. customdried under vacuum at 40° C.

出典と根拠

ORDレコード
ord-ee84b7cd54354a95a48086fd0327be91
出典データセット
uspto-grants-2005_02
特許番号
US06849738B2

反応ノート

読み込み中…