HRID589194

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID67184

1-Bromopyrrolidine-2,5-dione

C4H4BrNO2

结构：CC(C)(C)OC(=O)N1C2CCC1CN(c1cc(N(COCC[Si](C)(C)C)COCC[Si](C)(C)C)n3ncc(-c4ccc(-c5ccccc5)nc4)c3n1)C2

HCID67295265

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)N1C2CCC1CN(c1nc3c(-c4ccc(-c5ccccc5)nc4)cnn3c(N(COCC[Si](C)(C)C)COCC[Si](C)(C)C)c1Br)C2

HCID67294397

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

NBS (64 mg, 0.36 mmol) was added to a solution of tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (249 mg, 0.33 mmol) in DMF (6 mL). After stirring at room temperature for 1 h, the mixture was diluted with H2O and then extracted with ethyl acetate (×2). The combined organic layers were washed with brine and dried with Na2SO4. Evaporation and purification by column chromatography afforded tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate: LCMS tR=3.66 Min (5 min run, UV254nm). Mass calculated for M+H 836.3, observed m/z 836.06 (M+H).

WORKUP

后处理

extractionextracted with ethyl acetate (×2)
washThe combined organic layers were washed with brine
dry with materialdried with Na2SO4
customEvaporation and purification by column chromatography

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-d34f7b4388b741ff931cee734e861afd
来源数据集: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09227971B2
来源说明: uspto-grants-2016_01

反应 SMILES

C1C(=O)N([Br:8])C(=O)C1.[CH3:9][Si:10]([CH3:61])([CH3:60])[CH2:11][CH2:12][O:13][CH2:14][N:15]([CH2:52][O:53][CH2:54][CH2:55][Si:56]([CH3:59])([CH3:58])[CH3:57])[C:16]1[N:21]2[N:22]=[CH:23][C:24]([C:25]3[CH:26]=[N:27][C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:29][CH:30]=3)=[C:20]2[N:19]=[C:18]([N:37]2[CH2:43][CH:42]3[N:44]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH:39]([CH2:40][CH2:41]3)[CH2:38]2)[CH:17]=1>CN(C=O)C.O>[CH3:59][Si:56]([CH3:58])([CH3:57])[CH2:55][CH2:54][O:53][CH2:52][N:15]([CH2:14][O:13][CH2:12][CH2:11][Si:10]([CH3:9])([CH3:60])[CH3:61])[C:16]1[N:21]2[N:22]=[CH:23][C:24]([C:25]3[CH:26]=[N:27][C:28]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)=[CH:29][CH:30]=3)=[C:20]2[N:19]=[C:18]([N:37]2[CH2:38][CH:39]3[N:44]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH:42]([CH2:41][CH2:40]3)[CH2:43]2)[C:17]=1[Br:8]