HRID1434585

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：F[P-](F)(F)(F)(F)F.c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1

HCID2724699

PyBOP

C18H28F6N6OP2

HCID9924013

未命名化合物

HCID18385102

未命名化合物

PRODUCTS

生成物

结构：Cn1cc(C(=O)N2CCN(c3ccc(OCCCN4CCCCC4)cc3)CC2)c2cc(F)ccc21

HCID57935847

未命名化合物

收率 15.2%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

CONDITIONS

反应条件

温度: 120 °C

PROCEDURE

实验过程

A solution of 5-fluoro-1-methyl-1H-indole-3-carboxylic acid [WO 0071537 A1] (35 mg) and 1-(4-{[3-(1-piperidinyl)propyl]oxy}phenyl)piperazine (D11) (50 mg) in dichloromethane (1 ml) was treated with benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (94.4 mg) and heated in a microwave (CEM™ Discover microwave) at 120° C. for 5 min. The reaction mixture was concentrated in vacuo and purified on a SCX cartridge (2 g) eluting with methanol-aqueous ammonia (10:1) followed by mass directed auto preparative HPLC to give the title compound (12 mg). LCMS RT=2.49 min, 478 (M+H)+

WORKUP

后处理

concentrationThe reaction mixture was concentrated in vacuo
custompurified on a SCX cartridge (2 g)
washeluting with methanol-aqueous ammonia (10:1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-81824e8f11314bc1a7d9ea2905217a3d
来源数据集: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07615550B2
来源说明: uspto-grants-2009_11

反应 SMILES

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[C:12]([OH:14])=O.[N:15]1([CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)=[CH:27][CH:26]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[C:12]([N:34]1[CH2:35][CH2:36][N:31]([C:28]2[CH:27]=[CH:26][C:25]([O:24][CH2:23][CH2:22][CH2:21][N:15]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]3)=[CH:30][CH:29]=2)[CH2:32][CH2:33]1)=[O:14]