HRID526098

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID149026

Tetrafluoro-m-phenylenediamine dihydrochloride

C6H6Cl2F4N2

HCID66715127

未命名化合物

结构：CC(=O)c1cnc2ccc(Cl)nc2c1N[C@H]1CC[C@H](CN(C)C)CC1

HCID178467145

未命名化合物

PRODUCTS

生成物

结构：CC(=O)c1cnc2ccc(-c3cc(Cl)c(O)c(Cl)c3)nc2c1N[C@H]1CC[C@H](CN(C)C)CC1.Cl.Cl

HCID178467094

未命名化合物

收率 92.9%

PROCEDURE

实验过程

Following general procedure II, 1-(6-chloro-4-{trans-4-[(dimethylamino)methyl]cyclohexylamino}-1,5-naphthyridin-3-yl)ethanone (153 mg, 0.42 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (180 mg, 0.63 mmol) followed by formation of the dihydrochloride salt to afford the desired product (164 mg, 69%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 9.15 (s, 1H), 8.46 (d, J=9.0 Hz, 1H), 8.33 (d, J=9.0 Hz, 1H), 8.12 (s, 2H), 5.76-5.71 (m, 1H), 3.09 (d, J=6.6 Hz, 2H), 2.76 (s, 3H), 2.50-2.40 (m, 2H), 2.08-1.98 (m, 3H), 1.74-1.64 (m, 2H), 1.47-1.37 (m, 2H); ESI MS m/z 493 [M+H]+; HPLC>99% (AUC), tR=9.83 min.

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-b5241dddb0294a4780b29ab8b2ecb1b0
来源数据集: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09345709B2
来源说明: uspto-grants-2016_05

反应 SMILES

[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]2[NH:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([CH2:22][N:23]([CH3:25])[CH3:24])[CH2:18][CH2:17]1.[Cl:26][C:27]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[C:29]([Cl:42])[C:28]=1[OH:43].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>>[ClH:1].[ClH:26].[Cl:26][C:27]1[CH:32]=[C:31]([C:2]2[N:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]3[NH:15][C@H:16]2[CH2:17][CH2:18][C@H:19]([CH2:22][N:23]([CH3:24])[CH3:25])[CH2:20][CH2:21]2)[CH:30]=[C:29]([Cl:42])[C:28]=1[OH:43]