HRID713256

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID23676156

Sodium t-butoxide

C4H9NaO

HCID42948943

未命名化合物

结构：CC(C)(C)Nc1nc2c(nc1Cl)CN(Cc1ccccc1)CC2.O=C(O)C(F)(F)F

HCID131734016

未命名化合物

PRODUCTS

生成物

HCID6422

未命名化合物

收率 483.8%

结构：CC(C)(C)Nc1nc2c(nc1N1CCC(Oc3ccc(F)cc3F)CC1)CN(Cc1ccccc1)CC2

HCID118159278

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

结构：c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1

催化剂HCID634876

2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

C44H32P2

结构：O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd]

催化剂HCID9811564

Bis(dibenzylideneacetone)palladium

C51H42O3Pd2

溶剂HCID1140

Toluene

C7H8

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

A solution of sodium tert-butoxide (81 mg, 0.843 mmol), 6-benzyl-N-(tert-butyl)-3-chloro-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine TFA salt (125 mg, 0.281 mmol), Pd2(dba)3 (12.86 mg, 0.014 mmol), 4-(2,4-difluorophenoxyl)piperidine hydrochloride (84 mg, 0.337 mmol), and BINAP (17.50 mg, 0.028 mmol) in toluene (937 μL) was stirred at 90° C. overnight. The crude reaction mixture was diluted in DMF, filtered through a hydrophilic PTFE 0.45 μm filter (Millipore® Millex-LCR), and purified via HPLC Method A to give 6-benzyl-N-(tert-butyl)-3-(4-(2,4-difluorophenoxyl)piperidin-1-yl)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine as a TFA salt (155 mg).

WORKUP

后处理

customThe crude reaction mixture
filtrationfiltered through a hydrophilic PTFE 0.45 μm
filtrationfilter (Millipore® Millex-LCR)
custompurified via HPLC Method A

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-7295972bb4924c94a95f7b2c97f1bcfa
来源数据集: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09181249B2
来源说明: uspto-grants-2015_11

反应 SMILES

CC(C)([O-])C.[Na+].[OH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[O:9].[CH2:14]([N:21]1[CH2:30][CH2:29][C:28]2[C:23](=[N:24][C:25](Cl)=[C:26]([NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])[N:27]=2)[CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.[F:38][C:39]1[CH:51]=[C:50]([F:52])[CH:49]=[CH:48][C:40]=1[O:41][CH:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1>C1(C)C=CC=CC=1.CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH2:14]([N:21]1[CH2:30][CH2:29][C:28]2[C:23](=[N:24][C:25]([N:45]3[CH2:44][CH2:43][CH:42]([O:41][C:40]4[CH:48]=[CH:49][C:50]([F:52])=[CH:51][C:39]=4[F:38])[CH2:47][CH2:46]3)=[C:26]([NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])[N:27]=2)[CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:8]([OH:9])([C:10]([F:13])([F:12])[F:11])=[O:7]