1-Naphthyl trifluoromethanesulfonate → (10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[2-chloro-4-(3,4-dihydro-naphthalen-1-yl)-phenyl]-methanone

HRID 1793980노트

반응식

HRID 1793980 반응식
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20](B4OC(C)(C)C(C)(C)O4)=[CH:19][C:18]=3[Cl:32])=[O:16])[CH2:6][C:5]=12.FC(F)(F)S(O[C:39]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:42]=[CH:41][CH:40]=1)(=O)=O>>[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:42]4[C:43]5[C:48](=[CH:47][CH:46]=[CH:45][CH:44]=5)[CH2:39][CH2:40][CH:41]=4)=[CH:19][C:18]=3[Cl:32])=[O:16])[CH2:6][C:5]=12

참가 물질

3

반응물 2

HCID 3788841-Naphthyl trifluoromethanesulfonateHCID 22219716(10,11-Dihydro-5H-pyrrolo[2,1-c](1,4]benzodiazepin-10-yl)-[2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone

생성물 1

HCID 10297680(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[2-chloro-4-(3,4-dihydro-naphthalen-1-yl)-phenyl]-methanone수율 96.3%

실험 절차

(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone of Example 10, Step B (0.300 g, 0.668 mmol) and naphthalen-1-yl trifluoromethanesulfonate (0.205 g, 0.735 mmol) were reacted by the procedure described in Example 1, Step F. The crude product was purified by flash column chromatography on silica gel, eluting with 30% ethyl acetate in hexane to afford a clear oil. The oil was recrystallized from diethyl ether/petroleum ether to afford white crystals (0.290 g), m.p. 174–176° C.

후처리

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with 30% ethyl acetate in hexane
  3. customto afford a clear oil
  4. customThe oil was recrystallized from diethyl ether/petroleum ether

출처 및 근거

ORD 기록
ord-59c8aec5d758495ab0cb222e7adbc213
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022699B2

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