Sodium Carbonate → HCID 178462788, 화합물

HRID 1710385

반응식

HRID 1710385 반응식
[C:1]1([C:7]2[CH:8]=[C:9]3[N:15]=[C:14]([CH2:16][CH2:17][CH:18]4[NH:24][C:23](=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19]4)[NH:13][C:10]3=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrC1C=C2N=C(CCC3NC(=O)CCCC3)NC2=NC=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:52]([N:54]1[CH2:59][CH2:58][N:57]([S:60](C2C=CC(B3OC(C)(C)C(C)(C)O3)=CC=2)(=[O:62])=[O:61])[CH2:56][CH2:55]1)[CH3:53]>>[CH2:52]([N:54]1[CH2:59][CH2:58][N:57]([S:60]([C:4]2[CH:3]=[CH:2][C:1]([C:7]3[CH:8]=[C:9]4[N:15]=[C:14]([CH2:16][CH2:17][CH:18]5[NH:24][C:23](=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19]5)[NH:13][C:10]4=[N:11][CH:12]=3)=[CH:6][CH:5]=2)(=[O:61])=[O:62])[CH2:56][CH2:55]1)[CH3:53]

참가 물질

5

반응물 4

HCID 10340Sodium CarbonateHCID 23154454HCID 23154454, 화합물2회HCID 178516005HCID 178516005, 화합물2회HCID 178516006HCID 178516006, 화합물2회

생성물 1

HCID 178462788HCID 178462788, 화합물

실험 절차

The title compound is analogously synthesized as described for 7-[2-(6-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-azepan-2-one (compound B1) from 300 mg of 7-[2-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-azepan-2-one (compound C1), 2.67 ml of aqueous sodium carbonate solution (strength 2.0 M), 510 mg 1-ethyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonyl]-piperazine (compound C4), and 131 mg of trans-dichloro-bis(tricyclohexyl-phosphine)-palladium(II) at 110° C. for 18 hours. After aqueous work-up using 200 ml of dichloromethane and 75 ml of water, purification by chromatography on flash silica gel (eluent gradient dichloromethane/5-50 vol. % ethanol) yields 175 mg of the title compound as a waxy solid. ESI-MS: 511.3 (MH+). TLC: Rf=0.30 (dichloromethane/ethanol 8:1 parts by volume).

후처리

  1. custom200 ml of dichloromethane and 75 ml of water, purification by chromatography on flash silica gel (eluent gradient dichloromethane/5-50 vol. % ethanol)

출처 및 근거

ORD 기록
ord-b0b5ef96fe4e44108a9f1daa87a842d9
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790710B2

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