HRID415026

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID688090

Diphenyl N-cyanocarbonimidate

C14H10N2O2

结构：NCC#Cc1ccc2ncnc(Nc3ccc4c(cnn4Cc4cccc(F)c4)c3)c2c1

HCID66623580

未命名化合物

PRODUCTS

生成物

结构：N#CN=C(NCC#Cc1ccc2ncnc(Nc3ccc4c(cnn4Cc4cccc(F)c4)c3)c2c1)Oc1ccccc1

HCID178512320

未命名化合物

收率 49.6%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID3776

Isopropanol

C3H8O

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

[6-(3-Amino-prop-1-ynyl)-quinazolin-4-yl]-[1-(3-fluoro-benzyl)-1H-indazol-5-yl]-amine (280 mg, 0.663 mmol) is treated with diphenyl cyanocarbonimidate (163 mg, 1.031 equiv.) in a mixture of i-PrOH (12 ml) and THF (4 ml). Stir mixture overnight, then concentrate to dryness and chromatograph on silica (EtOAc/hexanes) to obtain 186.3 mg (49.6%) of pure desired product.

WORKUP

后处理

concentrationconcentrate to dryness and chromatograph on silica (EtOAc/hexanes)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-8ebe883f49de48acac0fddeee3c8c2b0
来源数据集: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08088766B2
来源说明: uspto-grants-2012_01

反应 SMILES

[NH2:1][CH2:2][C:3]#[C:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][N:9]=[C:8]2[NH:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=1)[N:20]=[CH:19]2.[CH:33]1[CH:38]=[CH:37][C:36]([O:39][C:40](OC2C=CC=CC=2)=[N:41][C:42]#[N:43])=[CH:35][CH:34]=1>CC(O)C.C1COCC1>[F:32][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=1)[CH2:25][N:21]1[C:22]2[C:18](=[CH:17][C:16]([NH:15][C:8]3[C:7]4[C:12](=[CH:13][CH:14]=[C:5]([C:4]#[C:3][CH2:2][NH:1][C:40](=[N:41][C:42]#[N:43])[O:39][C:36]5[CH:37]=[CH:38][CH:33]=[CH:34][CH:35]=5)[CH:6]=4)[N:11]=[CH:10][N:9]=3)=[CH:24][CH:23]=2)[CH:19]=[N:20]1