HRID246527

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6385

tert-Butylamine

C4H11N

HCID7912

Diisopropylamine

C6H15N

结构：CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F

HCID9886157

Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

C10H15F6N6OP

结构：CC(C)(C)OC(=O)N1CC(Cn2nc(-c3cnc4c(n3)c(C(=O)O)cn4COCC[Si](C)(C)C)c3ccc(F)cc32)C1

HCID71280170

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)NC(=O)c1cn(COCC[Si](C)(C)C)c2ncc(-c3nn(CC4CN(C(=O)OC(C)(C)C)C4)c4cc(F)ccc34)nc12

HCID71280418

未命名化合物

收率 91.7%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

2-(1-((1-(tert-butoxycarbonyl)azetidin-3-yl)methyl)-6-fluoro-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (150 mg, 251 μmol), 2-methylpropan-2-amine (18.4 mg, 251 μmol), HATU (105 mg, 277 μmol) and diisopropylamine (97.5 mg, 754 μmol) in dimethylformamide (12 mL) were stirred at room temperature for 15 h. The mixture was partitioned between ethyl acetate and water then the organic phase was washed with water then dried, filtered and concentrated in vacuo. Purification by chromatography (silica, 24 g Analogix column, 0-40% ethyl acetate in hexanes) gave tert-butyl 3-((3-(7-(tert-butylcarbamoyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)-6-fluoro-1H-indazol-1-yl)methyl)azetidine-1-carboxylate (150 mg, 91.5%).

WORKUP

后处理

customThe mixture was partitioned between ethyl acetate and water
washthe organic phase was washed with water
customthen dried
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by chromatography (silica, 24 g Analogix column, 0-40% ethyl acetate in hexanes)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-e8c825a0b8fc4336a8ec5634d79afc22
来源数据集: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08658646B2
来源说明: uspto-grants-2014_02

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=3)[C:15]([C:23]3[N:24]=[C:25]4[C:31]([C:32](O)=[O:33])=[CH:30][N:29]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[C:26]4=[N:27][CH:28]=3)=[N:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:43][C:44]([NH2:47])([CH3:46])[CH3:45].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(NC(C)C)(C)C>CN(C)C=O>[C:44]([NH:47][C:32]([C:31]1[C:25]2[C:26](=[N:27][CH:28]=[C:23]([C:15]3[C:16]4[C:21](=[CH:20][C:19]([F:22])=[CH:18][CH:17]=4)[N:13]([CH2:12][CH:10]4[CH2:11][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:9]4)[N:14]=3)[N:24]=2)[N:29]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:40])([CH3:41])[CH3:42])[CH:30]=1)=[O:33])([CH3:46])([CH3:45])[CH3:43]