HRID1744134

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8471

Triethylamine

C6H15N

HCID516892

Sodium Bicarbonate

CHNaO3

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

HCID2724699

PyBOP

C18H28F6N6OP2

HCID11491918

Acetonitrile, 2-amino-, hydrochloride (1:1)

C2H5ClN2

结构：CC(C)C[C@H](Nc1nn(C(=O)OC(C)(C)C)cc1-c1ccc(N2CCN(C(=O)OC(C)(C)C)CC2)cc1)C(=O)O

HCID69152735

未命名化合物

PRODUCTS

生成物

结构：CC(C)C[C@H](Nc1nn(C(=O)OC(C)(C)C)cc1-c1ccc(N2CCN(C(=O)OC(C)(C)C)CC2)cc1)C(=O)NCC#N

HCID86594575

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

To N-(1-(tert-butoxycarbonyl)-4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1H-pyrazol-3-yl)leucine (864 mg, 1.55 mmol), PyBOP (890 mg, 1.71 mmol), aminoacetonitrile hydrochloride (315 mg, 3.41 mmol) in dry DMF (40 mL) under dry nitrogen was added triethylamine (0.76 mL, 5.43 mmol) dropwise and the reaction was stirred for 4½ hours. Aqueous sat. NaHCO3 was added and the product extracted with Et2O (2×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (EtOAc/Hex, 4/6) to afford N1-(cyanomethyl)-N2-(1-(tert-butoxycarbonyl)-4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1H-pyrazol-3-yl)leucinamide.

WORKUP

后处理

extractionthe product extracted with Et2O (2×)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
custompurified by flash chromatography over silica gel (EtOAc/Hex, 4/6)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-4b2fe9ccf99c48c4b070e5dc1e1e8117
来源数据集: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07012075B2
来源说明: uspto-grants-2006_03

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[C:10]([NH:32][C@H:33]([C:38]([OH:40])=O)[CH2:34][CH:35]([CH3:37])[CH3:36])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CN([P+](O[N:58]2N=[N:65][C:60]3C=CC=C[C:59]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.NCC#N.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:59]([CH2:60][NH:65][C:38](=[O:40])[C@H:33]([CH2:34][CH:35]([CH3:36])[CH3:37])[NH:32][C:10]1[C:11]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:29])[CH3:30])=[O:26])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[CH:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[N:9]=1)#[N:58]