HCID 178433096, compound → HCID 178433087, compound

HRID 2377779Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22]=[C:21]3[C:17]([N:18]=[C:19]([C:23]4[C:24](=[O:40])[NH:25][CH:26]=[CH:27][C:28]=4[NH:29][CH2:30][C@H:31]([C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=4)[OH:32])[NH:20]3)=[C:16]([CH3:41])[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(Cl)Cl>[Cl:39][C:35]1[CH:34]=[C:33]([C@H:31]([OH:32])[CH2:30][NH:29][C:28]2[CH:27]=[CH:26][NH:25][C:24](=[O:40])[C:23]=2[C:19]2[NH:20][C:21]3[C:17]([N:18]=2)=[C:16]([CH3:41])[N:15]=[C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[N:22]=3)[CH:38]=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of 4-(8-{4-[2-(3-Chloro-phenyl)-2(S)-hydroxy-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-6-methyl-9H-purin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (72 mg, 0.124 mmol) in CH2Cl2 (30 mL) was added benzenesulfonyl fonctionalized silica gel, 0.79 meq/g (7.2 g). The heterogeneous mixture was stirred at 23° C. for 16 hours. The solvent was removed by filtration and the silica gel was washed with a mixture of ammonia 2N in MeOH:CH2Cl2 (1:1, 20 mL). The ammoniac solution was evaporated in vacuo to give the title compound as a light yellow solid. (0.053 g, 89%). HPLC 98%; LCMS (+ESI, M+H+) m/z 481; IR (KBr, cm−1) 3262, 2922, 1646, 1597, 1489, 1232; 1H NMR (400 MHz, DMSO+D2O) δ 10.80 (br s, 1H), 7.59-7.29 (m, 5H), 6.23 (d, J=8.2 Hz, 1H), 5.00 (br t, 1H), 3.75 (br s, 4H), 3.62 (m, 1H), 2.89 (br s, 4H), 2.60 (s, 3H); HRMS calcd for C23H25ClN8O2: 480.1789; found 480.1804.

Workup

customThe solvent was removed by filtration
washthe silica gel was washed with a mixture of ammonia 2N in MeOH:CH2Cl2 (1:1, 20 mL)
customThe ammoniac solution was evaporated in vacuo

Sources & evidence

ORD record: ord-29e31bd6bd6c45a38c8573418d3069bf
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470696B2

Reaction notes

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