HRID1909065

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID2724141

Tetra-n-butylammonium fluoride

C16H36FN

结构：CC(C)(C)OC(=O)n1ccc2c(-c3cc(C(=O)c4nc5ccc(N6CCC(O[Si](c7ccccc7)(c7ccccc7)C(C)(C)C)CC6)nc5[nH]4)ccc3C#N)cncc21

HCID178451568

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)n1ccc2c(-c3cc(C(=O)c4nc5ccc(N6CCC(O)CC6)nc5[nH]4)ccc3C#N)cncc21

HCID178451566

未命名化合物

收率 66%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

2 次

PROCEDURE

实验过程

To a solution of 4-(5-{5-[4-(tert-Butyl-diphenyl-silanyloxy)-piperidin-1-yl]-3H-imidazo[4,5-b]pyridine-2-carbonyl}-2-cyano-phenyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester in THF (0.2M) was added a 1M TBAF in THF solution at 23° C. After 24 hr, the reaction was quenched with sat'd NaHCO3 and extracted with EtOAc (3×), the combined organics washed with brine, dried over Na2SO4, filtered, and concentrated to a red solid. The crude was purified using chromatography eluting with MeOH/DCM mixtures giving 4-{2-Cyano-5-[5-(4-hydroxy-piperidin-1-yl)-3H-imidazo[4,5-b]pyridine-2-carbonyl]-phenyl}-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester as a red-orange solid (420 mg, 0.738 mmol, 66%). MS ESI m/z 564.5 (M+H)+.

WORKUP

后处理

customthe reaction was quenched with sat'd NaHCO3
extractionextracted with EtOAc (3×)
washthe combined organics washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated to a red solid
customThe crude was purified
washeluting with MeOH/DCM

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-890ca9d2bc7740ce9944e415faa980f5
来源数据集: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08598217B2
来源说明: uspto-grants-2013_12

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[C:12]2=[CH:13][N:14]=[CH:15][C:16]([C:17]3[CH:22]=[C:21]([C:23]([C:25]4[NH:57][C:28]5=[N:29][C:30]([N:33]6[CH2:38][CH2:37][CH:36]([O:39][Si](C(C)(C)C)(C7C=CC=CC=7)C7C=CC=CC=7)[CH2:35][CH2:34]6)=[CH:31][CH:32]=[C:27]5[N:26]=4)=[O:24])[CH:20]=[CH:19][C:18]=3[C:58]#[N:59])=[C:11]2[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:12]2=[CH:13][N:14]=[CH:15][C:16]([C:17]3[CH:22]=[C:21]([C:23]([C:25]4[NH:57][C:28]5=[N:29][C:30]([N:33]6[CH2:34][CH2:35][CH:36]([OH:39])[CH2:37][CH2:38]6)=[CH:31][CH:32]=[C:27]5[N:26]=4)=[O:24])[CH:20]=[CH:19][C:18]=3[C:58]#[N:59])=[C:11]2[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]