Benzyl (1S)-2-[(2-aminophenyl)amino]-1-[3-bromo-4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)benzyl]-2-oxoethylcarbamate → Benzyl (1S)-1-(1H-benzimidazol-2-yl)-2-[3-bromo-4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]ethylcarbamate

HRID 724663Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=O)[C@@H:10]([NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[S:22](=[O:24])(=[O:23])[NH:21][C:20](=[O:25])[CH2:19]2)=[C:14]([Br:26])[CH:13]=1>C(O)(=O)C>[NH:1]1[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N:8]=[C:9]1[C@@H:10]([NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[S:22](=[O:24])(=[O:23])[NH:21][C:20](=[O:25])[CH2:19]2)=[C:14]([Br:26])[CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Benzyl (1S)-2-[(2-aminophenyl)amino]-1-[3-bromo-4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)benzyl]-2-oxoethylcarbamate (28.2 mg, 0.0469 mmol) was dissolved in acetic acid (2.76 mL) and stirred at 60° C. for 1 h. The solution was concentrated and purified by preparative LCMS to afford product as a white solid (26.1 mg, 95%). 1H NMR (400 MHz, CD3OD): δ 7.79–7.56 (m, 5H), 7.42–7.12 (m, 7H), 5.61–5.57 (m, 1H), 5.35–5.31 (m, 1H), 5.03 (s, 2H), 3.47–3.28 (m, 1H); LCMS found for C26H24BrN4O5S (M+H)+: m/z=583.

Workup

concentrationThe solution was concentrated
custompurified by preparative LCMS

Sources & evidence

ORD record: ord-3f7661ce543b41aeadb39bb0dbfb8b6a
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

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