HRID2173616

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10796

Cesium carbonate

CCs2O3

HCID601894

4-Amino-7-nitrobenzofurazan

C6H4N4O3

结构：CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21

HCID636044

1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

C39H32OP2

结构：CC(C)(C)c1nc(N2CC[C@H](O)C2)c2nnn(Cc3cccnc3Cl)c2n1

HCID86295836

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)c1nc(N2CC[C@H](O)C2)c2nnn(Cc3cccnc3Nc3ccc([N+](=O)[O-])c4nonc34)c2n1

HCID86683341

未命名化合物

收率 16.5%

AUXILIARIES

试剂、催化剂与溶剂

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HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度: 120 °C

PROCEDURE

实验过程

A mixture of (S)-1-[5-tert-Butyl-3-(2-chloro-pyridin-3-ylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol (example 140) (5.30 mg, 13.7 μmol), 7-nitrobenzo[c][1,2,5]oxadiazol-4-amine (2.95 mg, 16.4 μmol), Pd2(dba)3 (1.25 mg, 1.37 μmol), xantphos (2.15 mg, 3.71 μmol) and Cs2CO3 (8.06 mg, 24.8 μmol) in dioxane (500 μl) was heated to 120° C. and stirred for 20 min. The crude material was filtered (celite), concentrated and purified by preparative HPLC eluting with a gradient formed from acetonitrile, water and NEt3. The product containing fractions were evaporated to yield 1.2 mg (16%) of the title compound as red solid. MS(m/e): 532.4 (MH+).

WORKUP

后处理

filtrationThe crude material was filtered (celite)
concentrationconcentrated
custompurified by preparative HPLC
washeluting with a gradient
customformed from acetonitrile, water and NEt3
additionThe product containing fractions
customwere evaporated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-32798b543ce94260b7bbd77c13db3057
来源数据集: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09056866B2
来源说明: uspto-grants-2015_06

反应 SMILES

[C:1]([C:5]1[N:6]=[C:7]([N:22]2[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23]2)[C:8]2[N:13]=[N:12][N:11]([CH2:14][C:15]3[C:16](Cl)=[N:17][CH:18]=[CH:19][CH:20]=3)[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].[N+:28]([C:31]1[C:36]2=[N:37][O:38][N:39]=[C:35]2[C:34]([NH2:40])=[CH:33][CH:32]=1)([O-:30])=[O:29].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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]>[C:1]([C:5]1[N:6]=[C:7]([N:22]2[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23]2)[C:8]2[N:13]=[N:12][N:11]([CH2:14][C:15]3[C:16]([NH:40][C:34]4[C:35]5=[N:39][O:38][N:37]=[C:36]5[C:31]([N+:28]([O-:30])=[O:29])=[CH:32][CH:33]=4)=[N:17][CH:18]=[CH:19][CH:20]=3)[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2]