HRID1063273

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

HCID516892

Sodium Bicarbonate

CHNaO3

HCID22278823

未命名化合物

结构：CCO[C@H]1CN(C(=O)OC)C[C@H]1Nc1nc(CC)c(I)nc1CC

HCID86591415

未命名化合物

PRODUCTS

生成物

结构：CCO[C@H]1CN(C(=O)OC)C[C@H]1Nc1nc(CC)c(-c2cc3c(cc2OC)CCC3)nc1CC

HCID24887777

未命名化合物

收率 95%

AUXILIARIES

试剂、催化剂与溶剂

结构：c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1

催化剂HCID178418397

未命名化合物

溶剂HCID8071

未命名化合物

CONDITIONS

反应条件

温度: 80 °C

PROCEDURE

实验过程

A 7 ml vial was charged with methyl (3R,4S)-3-[(3,6-diethyl-5-iodopyrazin-2-yl)amino]-4-ethoxypyrrolidine-1-carboxylate (100 mg), 6-methoxy-2,3-dihydro-1H-inden-5-ylboronic acid (82 mg) (Preparation 2), tetrakis(triphenylphosphine)palladium (20 mg), 2 M Na2CO3 (0.4 mL), and ethylene glycol dimethyl ether (1.6 mL). The reaction was stirred for 18 hours at 80° C. The reaction was poured into sat. aq. NaHCO3 and extracted with ethyl ether. The organic phases were combined, dried with MgSO4, filtered, and concentrated. The crude was purified with flash column chromatography (silica, a gradient of 10-25% EtOAc in heptane) to give 97 mg, 95% of methyl (3R,4S)-3-{[3,6-diethyl-5-(6-methoxy-2,3-dihydro-1H-inden-5-yl)pyrazin-2-yl]amino}-4-ethoxypyrrolidine-1-carboxylate. IR (diffuse reflectance) 2967, 2934, 2876, 2350, 2335, 2224, 2063, 1940, 1710, 1568, 1482, 1466, 1451, 1392, 1348 cm−1 HRMS (ESI) calcd for C26H36N4O4+H1 469.2815. found 469.2805. Anal. Calcd for C26H36N4O4: C, 66.64; H, 7.74; N, 11.96. Found: C, 66.27; H, 7.61; N, 11.75.

WORKUP

后处理

extractionextracted with ethyl ether
dry with materialdried with MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude was purified with flash column chromatography (silica

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-5e1612bd5e924a3ab4c5a0db44f991aa
来源数据集: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06964965B2
来源说明: uspto-grants-2005_11

反应 SMILES

[CH2:1]([C:3]1[C:4]([NH:12][C@H:13]2[C@@H:17]([O:18][CH2:19][CH3:20])[CH2:16][N:15]([C:21]([O:23][CH3:24])=[O:22])[CH2:14]2)=[N:5][C:6]([CH2:10][CH3:11])=[C:7](I)[N:8]=1)[CH3:2].[CH3:25][O:26][C:27]1[CH:35]=[C:34]2[C:30]([CH2:31][CH2:32][CH2:33]2)=[CH:29][C:28]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH2:1]([C:3]1[C:4]([NH:12][C@H:13]2[C@@H:17]([O:18][CH2:19][CH3:20])[CH2:16][N:15]([C:21]([O:23][CH3:24])=[O:22])[CH2:14]2)=[N:5][C:6]([CH2:10][CH3:11])=[C:7]([C:28]2[CH:29]=[C:30]3[C:34](=[CH:35][C:27]=2[O:26][CH3:25])[CH2:33][CH2:32][CH2:31]3)[N:8]=1)[CH3:2]