HRID30806

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

HCID3251421

Potassium bis(trimethylsilyl)amide

C6H18KNSi2

HCID69008397

未命名化合物

HCID86045323

未命名化合物

PRODUCTS

生成物

结构：CN1CCC(C(=O)Nc2cc(Oc3ccc4sc(Nc5cccc(C(C)(C)C)c5)nc4c3)ccn2)CC1

HCID59790078

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

The mixture containing 2-(3-tert-butylphenylamino)benzo[d]thiazol-5-ol (1 eq), potassium bis(trimethylsilyl)amide (4 eq), and potassium carbonate (1.2 eq) in dimethylformamide was stirred at room temperature for 10 minutes. N-(4-chloropyridin-2-yl)-1-methylpiperidine-4-carboxamide (1.4 eq) was then added and mixture subjected to microwave at 220° C. for 20 minutes. Reaction partitioned between ethyl acetate and water. Organic layer separated, washed with brine, dried over sodium sulfate and concentrated to give crude product. Purification by HPLC to yield N-[4-({2-[(3-tert-butylphenyl)amino]-1,3-benzothiazol-5-yl}oxy)pyridin-2-yl]-1-methylpiperidine-4-carboxamide. HPLC=4.74 min; MS: MH+=516.

WORKUP

后处理

waitto microwave at 220° C. for 20 minutes
customReaction
custompartitioned between ethyl acetate and water
customOrganic layer separated
washwashed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customto give crude product
customPurification by HPLC

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-4adb3169209d4cafaefd829c100a5310
来源数据集: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07423150B2
来源说明: uspto-grants-2008_09

反应 SMILES

[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[S:13][C:14]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:15]=3[N:16]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].C(=O)([O-])[O-].[K+].[K+].Cl[C:39]1[CH:44]=[CH:43][N:42]=[C:41]([NH:45][C:46]([CH:48]2[CH2:53][CH2:52][N:51]([CH3:54])[CH2:50][CH2:49]2)=[O:47])[CH:40]=1>CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[S:13][C:14]3[CH:20]=[CH:19][C:18]([O:21][C:39]4[CH:44]=[CH:43][N:42]=[C:41]([NH:45][C:46]([CH:48]5[CH2:53][CH2:52][N:51]([CH3:54])[CH2:50][CH2:49]5)=[O:47])[CH:40]=4)=[CH:17][C:15]=3[N:16]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]