HRID1931668

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID23145620

未命名化合物

2 次

结构：CC(C)c1noc(C2CCC(n3ncc4c(Oc5ccc(S(C)(=O)=O)cc5F)ncnc43)CC2)n1

HCID44514990

未命名化合物

结构：CC(C)(C)OC(=O)N1CCC(n2ncc3c(Cl)ncnc32)CC1

HCID57964905

未命名化合物

2 次

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)N1CCC(n2ncc3c(Oc4ccc(S(C)(=O)=O)c(F)c4)ncnc32)CC1

HCID57964934

未命名化合物

收率 43%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

4-[4-(3-Fluoro-4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester was prepared using the procedure described for the preparation of 4-(2-fluoro-4-methanesulfonyl-phenoxy)-1-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-cyclo-hexyl]-1H-pyrazolo[3,4-d]pyrimidine (Example 129) by the reaction of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19) with 3-fluoro-4-methanesulfonyl-phenol (Intermediate 2) in dimethylformamide. The product was purified by flash chromatography, eluting with 40% ethyl acetate/hexanes to give 4-[4-(3-fluoro-4-methanesulfonyl-phenoxy)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (75 mg, 43%) as a white solid. Mass spectrum: Observed 491.9.

WORKUP

后处理

custom4-[4-(3-Fluoro-4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester was prepared
customThe product was purified by flash chromatography
washeluting with 40% ethyl acetate/hexanes

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-11413fa2696c407aabf0014fd3df6d78
来源数据集: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08188098B2
来源说明: uspto-grants-2012_05

反应 SMILES

FC1C=C(S(C)(=O)=O)C=CC=1OC1N=CN=C2N(C3CCC(C4ON=C(C(C)C)N=4)CC3)N=CC=12.[C:36]([O:40][C:41]([N:43]1[CH2:48][CH2:47][CH:46]([N:49]2[C:53]3=[N:54][CH:55]=[N:56][C:57](Cl)=[C:52]3[CH:51]=[N:50]2)[CH2:45][CH2:44]1)=[O:42])([CH3:39])([CH3:38])[CH3:37].[F:59][C:60]1[CH:61]=[C:62]([OH:70])[CH:63]=[CH:64][C:65]=1[S:66]([CH3:69])(=[O:68])=[O:67]>CN(C)C=O>[C:36]([O:40][C:41]([N:43]1[CH2:48][CH2:47][CH:46]([N:49]2[C:53]3=[N:54][CH:55]=[N:56][C:57]([O:70][C:62]4[CH:63]=[CH:64][C:65]([S:66]([CH3:69])(=[O:68])=[O:67])=[C:60]([F:59])[CH:61]=4)=[C:52]3[CH:51]=[N:50]2)[CH2:45][CH2:44]1)=[O:42])([CH3:39])([CH3:38])[CH3:37]