Pyridine → Sufugolix

HRID 23255노트

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HRID 23255 반응식
[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

참가 물질

7

반응물 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

생성물 1

HCID 3038517Sufugolix수율 98.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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%).

후처리

  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.

출처 및 근거

ORD 기록
ord-ee84b7cd54354a95a48086fd0327be91
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849738B2

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