Sodium Carbonate → (S)-3-(Methylsulfonamido)-5-(4-((1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl methanesulfonate

HRID 1052483노트

반응식

HRID 1052483 반응식
Br[C:2]1[C:10]2[C:9]([NH:11][C@H:12]([C:14]3[N:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:18](=[O:26])[C:17]4=[CH:27][CH:28]=[CH:29][N:16]4[N:15]=3)[CH3:13])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:3]=1.[CH3:38][S:39]([O:42][C:43]1[CH:48]=[C:47](B2OC(C)(C)C(C)(C)O2)[CH:46]=[C:45]([NH:58][S:59]([CH3:62])(=[O:61])=[O:60])[CH:44]=1)(=[O:41])=[O:40].CS(Cl)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:38][S:39]([O:42][C:43]1[CH:48]=[C:47]([C:2]2[C:10]3[C:9]([NH:11][C@H:12]([C:14]4[N:19]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[C:18](=[O:26])[C:17]5=[CH:27][CH:28]=[CH:29][N:16]5[N:15]=4)[CH3:13])=[N:8][CH:7]=[N:6][C:5]=3[N:4]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:3]=2)[CH:46]=[C:45]([NH:58][S:59]([CH3:62])(=[O:61])=[O:60])[CH:44]=1)(=[O:40])=[O:41]

참가 물질

6

반응물 4

HCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 901035453-(Methylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl methanesulfonateHCID 131736160(S)-2-(1-((5-Bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

생성물 1

HCID 131736165(S)-3-(Methylsulfonamido)-5-(4-((1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl methanesulfonate

시약·촉매·용매 1

HCID 178418476HCID 178418476, 화합물촉매

실험 절차

(S)-2-(1-((5-Bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (170 mg, 0.29 mmol) was treated with 3-(methylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl methanesulfonate (230 mg, 0.73 mmol, prepared from the title compound of Preparation 105 and methanesulfonyl chloride according to Preparation 37), sodium carbonate (95 mg, 3.06 mmols) and bis(triphenylphosphine)palladium(II) dichloride (70 mg, 0.09 mmol) according to the method described in Preparation 62. The residue was purified using SP1® Purification System (0% to 80%, hexane-ethyl acetate) to give 82 mg (37% yield) of the title compound. Purity 98%.

출처 및 근거

ORD 기록
ord-f63c451080a1436694567c7fabab7ad4
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388189B2

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