HRID1850591

反应详情

EQUATION

反应方程式

REACTANTS

反应物

反应SMILES：CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)O

HCID85083

1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

C10H17NO4

反应SMILES：CN(C)C(=O)c1cc2cnc(Nc3ccc(C(=O)N4CC5CCC(C4)N5)cn3)nc2n1C1CCCC1

HCID53378674

未命名化合物

PRODUCTS

产物

反应SMILES：CN(C)C(=O)c1cc2cnc(Nc3ccc(C(=O)N4CC5CCC(C4)N5C(=O)C4CCCN4C(=O)OC(C)(C)C)cn3)nc2n1C1CCCC1

HCID67356816

未命名化合物

收率 67.6%

PROCEDURE

实验过程

Following general amide formation method 1, 7-cyclopentyl-2-[5-(3,8-diaza-bicyclo[3.2.1]octane-3-carbonyl)-pyridin-2-ylamino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (100 mg, 0.205 mmol, 1.0 eq) was combined with BOC-Proline (48.5 mg, 0.225 mmol, 1.1 eq) which gave 2-{3-[6-(7-Cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridine-3-carbonyl]-3,8-diaza-bicyclo[3.2.1]octane-8-carbonyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (95 mg) in 64% yield. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.36-1.57 (m, 12H) 1.63-1.86 (m, 5H) 1.91 (br. s., 4H) 1.99-2.29 (m, 10H) 2.45-2.67 (m, 2H) 3.18 (s, 7H) 3.43 (d, J=6.57 Hz, 2H) 3.60 (br. s., 3H) 4.42 (br. s., 2H) 4.56 (br. s., 2H) 4.68-4.94 (m, 2H) 6.53 (s, 1H) 7.83 (d, J=8.08 Hz, 1H) 8.41 (br. s., 1H) 8.58 (d, J=8.59 Hz, 1H) 8.76-8.80 (m, 1H). HRMS m/z, (M+H)+: 686.3769.

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-1fe476e3857845a1a35ea0190b939513
来源数据集: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US08957074B2
来源说明: uspto-grants-2015_02

反应SMILES

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