N-bromobutanimide → HCID 135955153, compound

HRID 600597Notes

Reaction equation

HRID 600597 reaction equation
[CH2:1]([C:8]1[N:12]=[C:11]([CH2:13][CH2:14][C:15]2[N:26]=[C:25]3[N:17]([C:18](=[O:31])[N:19]([CH2:27][CH2:28][CH2:29][CH3:30])[C:20]4[N:21]=[CH:22][NH:23][C:24]=43)[N:16]=2)[O:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:32]N1C(=O)CCC1=O>C1COCC1>[CH2:1]([C:8]1[N:12]=[C:11]([CH2:13][CH2:14][C:15]2[N:26]=[C:25]3[N:17]([C:18](=[O:31])[N:19]([CH2:27][CH2:28][CH2:29][CH3:30])[C:20]4[N:21]=[C:22]([Br:32])[NH:23][C:24]=43)[N:16]=2)[O:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 135984685HCID 135984685, compound

Product 1

HCID 135955153HCID 135955153, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 8-[2-(3-benzyl-1,2,4-oxadiazol-5-yl)ethyl]-4-butyl-1,4-dihydro-5H-[1,2,4]triazolo[5,1-i]purin-5-one (40 mg, 0.096 mmol) in THF (5 mL) was added N-bromosuccinimide (19 mg, 0.11 mmol). After stirring at room temperature overnight, the reaction was quenched with phenol. The reaction mixture was concentrated, and the residue was purified by preparative LCMS (method A) to give desired product as white powder. LCMS calculated for C21H22BrN8O2(M+H): 497.1. found: 497.0, 499.0.

Workup

  1. customthe reaction was quenched with phenol
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by preparative LCMS (method A)

Sources & evidence

ORD record
ord-b24345f4253c4ad2bf6b37ce701381f3
Source dataset
uspto-grants-2011_03
Patent number
US07902205B2

Reaction notes

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