N-bromobutanimide → N-[(7-bromo-5-oxo-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-3-yl)methyl]benzamide

HRID 1664572Notes

Reaction equation

[O:1]=[C:2]1[N:10]2[C:11]([CH2:14][NH:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:12][N:13]=[C:9]2[N:8]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:7]2[N:6]=[CH:5][NH:4][C:3]1=2.[Br:29]N1C(=O)CCC1=O>C1COCC1>[Br:29][C:5]1[NH:4][C:3]2[C:2](=[O:1])[N:10]3[C:11]([CH2:14][NH:15][C:16](=[O:23])[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[N:12][N:13]=[C:9]3[N:8]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:7]=2[N:6]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To the solution of N-[(5-oxo-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-3-yl)methyl]benzamide (0.11 g, 0.28 mmol) in THF (10 mL) was added N-Bromosuccinimide (0.076 g, 0.42 mmol). The mixture was stirred at 70° C. for 1 hour. The reaction mixture was concentrated and purified by preparative LCMS. LCMS calculated for C19H21BrN7O2 (M+H): 458.1. found: 458.0, 460.0.

Workup

concentrationThe reaction mixture was concentrated
custompurified by preparative LCMS

Sources & evidence

ORD record: ord-3959ecef6d7a4b0eb8f992fdb285d1f8
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039478B2

Reaction notes

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