HRID1499521

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID81531

Diisopropylethylamine

C8H19N

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)Nc1sc(-c2c(F)cccc2F)nc1C(=O)O

HCID67438198

5-[(tert-Butoxycarbonyl)amino]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxylic acid

C15H14F2N2O4S

结构：CC(=O)OC1CCc2c1ncc(N)c2N1C[C@H](C)C[C@H](NC(=O)OC(C)(C)C)C1

HCID86726748

未命名化合物

PRODUCTS

生成物

结构：CC(=O)OC1CCc2c1ncc(NC(=O)c1nc(-c3c(F)cccc3F)sc1NC(=O)OC(C)(C)C)c2N1C[C@H](C)C[C@H](NC(=O)OC(C)(C)C)C1

HCID86726752

未命名化合物

收率 52.2%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID887

Methanol

CH4O

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

A mixture of 3-amino-4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate (13.0 mg, 0.032 mmol), 5-[(tert-butoxycarbonyl)amino]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxylic acid (13.7 mg, 0.040 mmol), HATU (30.5 mg, 0.080 mmol) in DMF (0.09 mL) and DIPEA (12.5 mg, 0.096 mmol) was stirred at room temperature for 16 h. The reaction mixture was diluted with MeOH and purified by preparative LC-MS (XBridge™ preparative C18 5 μm OBD™ column, 30×10 mm, 60 mL/min., eluting with a gradient of MeCN and water with 0.1% NH4OH) to give the sub-title compound as a white powder (12.4 mg, 52%). LCMS calc. for C36H45F2N6O7S (M+H)+: m/z=743.3. Found: 743.3.

WORKUP

后处理

custompurified by preparative LC-MS (XBridge™ preparative C18 5 μm OBD™ column, 30×10 mm, 60 mL/min.
washeluting with a gradient of MeCN and water with 0.1% NH4OH)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c22eeb1afc424ed09ceb37390fcdb4d8
来源数据集: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09200004B2
来源说明: uspto-grants-2015_12

反应 SMILES

[C:1]([O:4][CH:5]1[C:9]2=[N:10][CH:11]=[C:12]([NH2:29])[C:13]([N:14]3[CH2:19][C@H:18]([CH3:20])[CH2:17][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:15]3)=[C:8]2[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[C:30]([O:34][C:35]([NH:37][C:38]1[S:42][C:41]([C:43]2[C:48]([F:49])=[CH:47][CH:46]=[CH:45][C:44]=2[F:50])=[N:40][C:39]=1[C:51](O)=[O:52])=[O:36])([CH3:33])([CH3:32])[CH3:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CO>[C:1]([O:4][CH:5]1[C:9]2=[N:10][CH:11]=[C:12]([NH:29][C:51]([C:39]3[N:40]=[C:41]([C:43]4[C:48]([F:49])=[CH:47][CH:46]=[CH:45][C:44]=4[F:50])[S:42][C:38]=3[NH:37][C:35]([O:34][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:36])=[O:52])[C:13]([N:14]3[CH2:19][C@H:18]([CH3:20])[CH2:17][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:15]3)=[C:8]2[CH2:7][CH2:6]1)(=[O:3])[CH3:2]