Water → 5-Bromo-8-(4-methylpiperazin-1-yl)tetrazolo[1,5-a]pyrazine

HRID 535708Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]3[N:10]([N:14]=[N:15][N:16]=3)[CH:11]=[CH:12][N:13]=2)[CH2:4][CH2:3]1.[Br:17]N1C(=O)CCC1=O.O.C(N(CC)CC)C>C(O)(=O)C>[Br:17][C:11]1[N:10]2[N:14]=[N:15][N:16]=[C:9]2[C:8]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)=[N:13][CH:12]=1

Participants

Conditions

Temperature: 35 °C

Procedure

8-(4-Methylpiperazin-1-yl)tetrazolo[1,5-a]pyrazine (100 g, 0.456 mol, 1.0 eq.) was suspended in acetic acid (110 ml) under nitrogen and stirred at 35° C. until a solution was obtained. The solution was cooled to 16° C. and N-Bromosuccinimide (82.14 g, 0.461 mol, 1.01 eq.) is added at such a rate that the temperature of the reaction was maintained at 14-18° C. The reaction was monitored and additional aliquots of N-bromosuccinimide added as necessary to ensure conversion was ≧99.5% after 2-3 hours stirring at 20° C. stirring. Water was added, and the solution is cooled to 13° C. The pH of the suspension is adjusted to 8.3-8.5 by addition of triethylamine. The resulting suspension was filtered, washed with water, and dried to afford the desired product (136.02 g, 100% yield).

Workup

customwas obtained
temperatureThe solution was cooled to 16° C.
temperaturewas maintained at 14-18° C
customafter 2-3 hours
stirringstirring at 20° C.
stirringstirring
temperaturethe solution is cooled to 13° C
filtrationThe resulting suspension was filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-8350dc92155848e1a3bc2244bafb2b62
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859550B2

Reaction notes

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