2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → (9H-fluoren-9-yl)methyl 2-((3-(4-(2-hydroxypropan-2-yl)phenyl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)methoxy)ethylcarbamate

HRID 1628101

반응식

HRID 1628101 반응식
COC1C=CC(C[O:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]([CH2:40][O:41][CH2:42][CH2:43][NH:44][C:45](=[O:61])[O:46][CH2:47][CH:48]4[C:60]5[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=5[C:54]5[C:49]4=[CH:50][CH:51]=[CH:52][CH:53]=5)[N:21]4[C:26]5[CH:27]=[CH:28][N:29]([S:30]([C:33]6[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=6)(=[O:32])=[O:31])[C:25]=5[N:24]=[CH:23][C:22]=34)=[CH:14][CH:13]=2)([CH3:11])[CH3:10])=CC=1.COC1C=CC(COC(C2C=CC([Mg]Br)=CC=2)(C)C)=CC=1.C1C2C(COC(NCCOCC(O)=O)=O)C3C(=CC=CC=3)C=2C=CC=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl.FC(F)(F)C([O-])=O.[Hg+2].FC(F)(F)C([O-])=O.O>[OH:8][C:9]([C:12]1[CH:13]=[CH:14][C:15]([C:18]2[N:19]=[C:20]([CH2:40][O:41][CH2:42][CH2:43][NH:44][C:45](=[O:61])[O:46][CH2:47][CH:48]3[C:49]4[CH:50]=[CH:51][CH:52]=[CH:53][C:54]=4[C:55]4[C:60]3=[CH:59][CH:58]=[CH:57][CH:56]=4)[N:21]3[C:26]4[CH:27]=[CH:28][N:29]([S:30]([C:33]5[CH:34]=[CH:35][C:36]([CH3:37])=[CH:38][CH:39]=5)(=[O:32])=[O:31])[C:25]=4[N:24]=[CH:23][C:22]=23)=[CH:16][CH:17]=1)([CH3:10])[CH3:11]

참가 물질

8

반응물 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 455991832-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)ethoxy)acetic acidHCID 67362121(9H-fluoren-9-yl)methyl 2-((3-(4-(2-(4-methoxybenzyloxy)propan-2-yl)phenyl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)methoxy)ethylcarbamateHCID 178491445HCID 178491445, 화합물

생성물 1

HCID 67216957(9H-fluoren-9-yl)methyl 2-((3-(4-(2-hydroxypropan-2-yl)phenyl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)methoxy)ethylcarbamate수율 45%

시약·촉매·용매 3

HCID 2723924Mercury bis(trifluoroacetate)촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a solution of (9H-fluoren-9-yl)methyl 2-((3-(4-(2-(4-methoxybenzyloxy)propan-2-yl)phenyl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)methoxy)ethylcarbamate (0.077 g, 0.089 mmol, prepared using AF from Example #2, Step B cyano intermediate with ((4-(2-(4-methoxybenzyloxy)propan-2-yl)phenyl)magnesium bromide [NOVEL], AG, J.1 with 2-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)ethoxy)acetic acid [Chem Impex] and L.1 with mercury(II) trifluoroacetate) in DCM (0.94 mL) and Water (0.05 mL) was added DDQ (0.030 gg, 0.134 mmol). The mixture was stirred at rt for about 45 min. The mixture was directly purified by flash chromatography (12 g silica gel column, 35 to 100% EtOAc/heptane) to give (9H-fluoren-9-yl)methyl 2-((3-(4-(2-hydroxypropan-2-yl)phenyl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)methoxy)ethylcarbamate (0.03 g, 45%): LC/MS (Table 2, Method b) Rt=2.90 min.; MS m/z: 742 (M+H)+.

후처리

  1. customThe mixture was directly purified by flash chromatography (12 g silica gel column, 35 to 100% EtOAc/heptane)

출처 및 근거

ORD 기록
ord-5d002257b52e4a059c6d6de3211b1b80
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785639B2

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