Water → (S)-N-(4-aminophenyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4, 3-a][1,4]diazepine-6-acetamide

HRID 727264

반응식

HRID 727264 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[C@H:10]([CH2:24][C:25](O)=[O:26])[N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:35]1[C:40]([NH2:41])=[CH:39][CH:38]=[C:37]([NH2:42])[CH:36]=1.O>CN(C)C=O>[NH2:41][C:40]1[CH:35]=[CH:36][C:37]([NH:42][C:25](=[O:26])[CH2:24][C@@H:10]2[N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]23)=[CH:38][CH:39]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7814P-PhenylenediamineHCID 8471TriethylamineHCID 668281072-((9S)-7-(4-chlorophenyl)-4,5,13-trimethyl-3-thia-1,8,11,12-tetraazatricyclo(8.3.0.0,2,6)trideca-2(6),4,7,10,12-pentaen-9-yl)acetic acid

생성물 1

HCID 68972164(S)-N-(4-aminophenyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4, 3-a][1,4]diazepine-6-acetamide수율 15.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(S)-4-(4-Chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f]-[1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetic acid (3.0 g), triethylamine (1.56 ml) and p-phenylenediamine (0.97 g) are dissolved in dimethylformamide (30 ml). Benzotriazol-1-yl-oxy-tris(dimethyl)phosphonium hexafluorophosphate (3.6 g) is added, and the mixture is stirred at room temperature for 12 hours. After the completion of the reaction, water (200 ml) is added, and the mixture is extracted with ethyl acetate. The extract is washed with saturated brine and dried over anhydrous magnesium sulfate. After the solvent is distilled away under reduced pressure, the residue is subjected to silica gel column chromatography and obtained crystals are recrystallized from toluene to give 0.56 g of (S)-N-(4-aminophenyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4, 3-a][1,4]diazepine-6-acetamide, melting point 169°-173° C.

후처리

  1. additionis added
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe extract is washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent is distilled away under reduced pressure
  6. customobtained crystals
  7. customare recrystallized from toluene

출처 및 근거

ORD 기록
ord-ead28fc17d244738af9fd38d986aa4a3
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05712274

연결된 노트

불러오는 중…