N-bromobutanimide → HCID 58173312, compound

HRID 2047155Notes

Reaction equation

HRID 2047155 reaction equation
C1C(=O)N([Br:8])C(=O)C1.C(O)=O.[NH2:12][C:13]1[N:18]2[N:19]=[CH:20][C:21]([C:22]3[CH:23]=[N:24][C:25]4[C:30]([CH:31]=3)=[CH:29][CH:28]=[CH:27][CH:26]=4)=[C:17]2[N:16]=[C:15]([N:32]2[CH2:38][CH2:37][C:36](=[O:39])[NH:35][CH2:34][CH2:33]2)[CH:14]=1>CC#N>[NH2:12][C:13]1[N:18]2[N:19]=[CH:20][C:21]([C:22]3[CH:23]=[N:24][C:25]4[C:30]([CH:31]=3)=[CH:29][CH:28]=[CH:27][CH:26]=4)=[C:17]2[N:16]=[C:15]([N:32]2[CH2:38][CH2:37][C:36](=[O:39])[NH:35][CH2:34][CH2:33]2)[C:14]=1[Br:8]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67494546HCID 67494546, compound

Product 1

HCID 58173312HCID 58173312, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of NBS (14.6 mg, 0.082 mmoL) in CH3CN (0.5 mL) was added to a mixture of 1-(7-amino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1,4-diazepan-5-one formic acid salt (32.3 mg, 0.077 mmoL) in CH3CN (3 mL). After stirring at room temperature for 10 min, the solvent was evaporated and the residue was purified by prep-LC to afford titled compound (22.6 mg, 59%). LCMS tR=2.78 Min. Mass calculated for, M+ 451.0, observed LC/MS m/z 452.0 (M+H).

Workup

  1. customthe solvent was evaporated
  2. customthe residue was purified by prep-LC

Sources & evidence

ORD record
ord-cfb085cfba1b43c9b2593be43614ec10
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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