N-bromobutanimide → HCID 58173435, compound

HRID 2047011Notes

Reaction equation

HRID 2047011 reaction equation
[Br:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[N:15]2[N:16]=[CH:17][C:18]([C:19]3[CH:20]=[N:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:14]2[N:13]=[C:12]([CH:29]2[CH2:34][NH:33][CH:32]([C:35]([O:37][CH3:38])=[O:36])[CH2:31][CH2:30]2)[CH:11]=1>C(#N)C.CO>[NH2:9][C:10]1[N:15]2[N:16]=[CH:17][C:18]([C:19]3[CH:20]=[N:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:14]2[N:13]=[C:12]([CH:29]2[CH2:34][NH:33][CH:32]([C:35]([O:37][CH3:38])=[O:36])[CH2:31][CH2:30]2)[C:11]=1[Br:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 58173554HCID 58173554, compound

Product 1

HCID 58173435HCID 58173435, compoundYield 18.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

N-bromosuccinimide (44 mg, 0.249 mmol) was added into a solution of methyl 5-(7-amino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidine-2-carboxylate (100 mg, 0.249 mmol) in acetonitrile (1.5 mL) and methanol (0.5 ml). The resulting solution is stirred at room temperature for 1 hour. The reaction was concentrated in vacuo and purified by prep-LC to afford the title compound (22.32 mg): LC/MS RT=2.56 min. Mass calculated for, M+H 481.09, observed 481.09.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by prep-LC

Sources & evidence

ORD record
ord-a698eed95a294231a2ef54862a2e2cdf
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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