HRID1486127

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID81531

Diisopropylethylamine

C8H19N

结构：CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[P-](F)(F)(F)(F)F

HCID2733084

Methanaminium, N-[(1H-benzotriazol-1-yloxy)(dimethylamino)methylene]-N-methyl-, hexafluorophosphate(1-) (1:1)

C11H16F6N5OP

HCID7009590

未命名化合物

结构：C[C@H]1[C@H](N)C(=O)N(Cc2c(C3CC3)cnc3ccccc23)c2ccc(C#N)cc2N1C(=O)C1CCOCC1.Cl.Cl

HCID90082427

未命名化合物

PRODUCTS

生成物

结构：C[C@@H](C(=O)N[C@@H]1C(=O)N(Cc2c(C3CC3)cnc3ccccc23)c2ccc(C#N)cc2N(C(=O)C2CCOCC2)[C@H]1C)N(C)C(=O)OC(C)(C)C

HCID118292686

未命名化合物

收率 77.3%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

To a 0° C. solution of (3S,4S)-3-amino-1-((3-cyclopropylquinolin-4-yl)methyl)-4-methyl-2-oxo-5-(tetrahydro-2H-pyran-4-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbonitrile dihydrochloride (60 mg, 103 μmol) in DMF (343 μl) was added Boc-N-methyl-L-alanine (23.0 mg, 113 μmol), N,N-diisopropylethylamine (89.1 μl, 515 μmol), and HBTU (43.0 mg, 113 μmol). The reaction was stirred at rt for 30 min, then diluted with EtOAc, washed with H2O, sat. aq. NaHCO3, and sat. aq. NaCl, dried over Na2SO4, filtered, and concentrated. The crude material was purified by flash chromatography to provide tert-butyl(S)-1-((3S,4S)-7-cyano-1-((3-cyclopropylquinolin-4-yl)methyl)-4-methyl-2-oxo-5-(tetrahydro-2H-pyran-4-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (55.3 mg, 77%) as a white solid. MS m/z 695 (MH)+.

WORKUP

后处理

washwashed with H2O, sat. aq. NaHCO3, and sat. aq. NaCl
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude material was purified by flash chromatography

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-6b282e741e5643b38e0cb7a4f363af23
来源数据集: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09422331B2
来源说明: uspto-grants-2016_08

反应 SMILES

Cl.Cl.[NH2:3][C@@H:4]1[C:10](=[O:11])[N:9]([CH2:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[CH:15][C:14]=2[CH:23]2[CH2:25][CH2:24]2)[C:8]2[CH:26]=[CH:27][C:28]([C:30]#[N:31])=[CH:29][C:7]=2[N:6]([C:32]([CH:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)=[O:33])[C@H:5]1[CH3:40].[C:41]([N:48]([CH3:54])[C@H:49]([C:51](O)=[O:52])[CH3:50])([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[C:30]([C:28]1[CH:27]=[CH:26][C:8]2[N:9]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]=[CH:15][C:14]=3[CH:23]3[CH2:25][CH2:24]3)[C:10](=[O:11])[C@@H:4]([NH:3][C:51](=[O:52])[C@@H:49]([N:48]([CH3:54])[C:41](=[O:42])[O:43][C:44]([CH3:45])([CH3:47])[CH3:46])[CH3:50])[C@H:5]([CH3:40])[N:6]([C:32]([CH:34]3[CH2:35][CH2:36][O:37][CH2:38][CH2:39]3)=[O:33])[C:7]=2[CH:29]=1)#[N:31]