HRID245760

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CCC[C@H](C)OC(=O)Nc1ccc(B2OC(C)(C)C(C)(C)O2)cc1OC

HCID67364014

未命名化合物

结构：CC(=O)NC[C@H]1CC[C@H](c2nc(Br)c3c(C)nccn32)CC1

HCID178474841

未命名化合物

PRODUCTS

生成物

结构：CCC[C@H](C)OC(=O)Nc1ccc(-c2nc([C@H]3CC[C@H](CNC(C)=O)CC3)n3ccnc(C)c23)cc1OC

HCID178448290

未命名化合物

收率 56%

PROCEDURE

实验过程

(S)-Pentan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl-carbamate (20 mg) and N-(((trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)methyl)acetamide (20 mg) were reacted according to the procedure described in example 4 step 4c and purified by prep-HPLC (column Luna C18(2); gradient acetonitrile/water with constant 0.003M trifluoroacetic acid). Proper fractions were collected and made basic with aqueous sodium hydrogencarbonate, extracted with dichloromethane, organic layer dried (Na2SO4) and concentrated in vacuo to give (S)-pentan-2-yl 4-(3-((trans)-4-(acetamidomethyl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate (16 mg).

WORKUP

后处理

custompurified by prep-HPLC (column Luna C18(2); gradient acetonitrile/water with constant 0.003M trifluoroacetic acid)
customProper fractions were collected
extractionextracted with dichloromethane, organic layer
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-5d87fcf60460465b9962508217c4528b
来源数据集: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08658794B2
来源说明: uspto-grants-2014_02

反应 SMILES

[CH3:1][O:2][C:3]1[CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=[CH:5][C:4]=1[NH:18][C:19](=[O:26])[O:20][C@H:21]([CH2:23][CH2:24][CH3:25])[CH3:22].Br[C:28]1[N:29]=[C:30]([C@H:38]2[CH2:43][CH2:42][C@H:41]([CH2:44][NH:45][C:46](=[O:48])[CH3:47])[CH2:40][CH2:39]2)[N:31]2[CH:36]=[CH:35][N:34]=[C:33]([CH3:37])[C:32]=12>>[C:46]([NH:45][CH2:44][C@H:41]1[CH2:40][CH2:39][C@H:38]([C:30]2[N:31]3[CH:36]=[CH:35][N:34]=[C:33]([CH3:37])[C:32]3=[C:28]([C:7]3[CH:6]=[CH:5][C:4]([NH:18][C:19](=[O:26])[O:20][C@H:21]([CH2:23][CH2:24][CH3:25])[CH3:22])=[C:3]([O:2][CH3:1])[CH:8]=3)[N:29]=2)[CH2:43][CH2:42]1)(=[O:48])[CH3:47]