N-bromobutanimide → HCID 46947712, compound

HRID 2047189Notes

Reaction equation

HRID 2047189 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[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]([C:29]2[CH:34]=[CH:33][C:32]([CH2:35][C:36]([OH:38])=[O:37])=[CH:31][CH:30]=2)[CH:11]=1>CC#N>[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]([C:29]2[CH:34]=[CH:33][C:32]([CH2:35][C:36]([OH:38])=[O:37])=[CH:31][CH:30]=2)[C:11]=1[Br:8]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66738932HCID 66738932, compound

Product 1

HCID 46947712HCID 46947712, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of NBS (32 mg, 0.179 mmol) in CH3CN (1 mL) was added to a mixture of [4-(7-amino-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-5-yl)-phenyl]-acetic acid (70 mg, 0.179 mmol) in CH3CN (3 mL). After stirring at room temperature for 1 h, the solvent was evaporated in vacuo and the residue was purified by prep-LC to afford titled compound (22.9 mg, 27%). LC/MS RT=3.44 min. Mass calculated for, M+H 474.05, observed 474.05.

Workup

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

Sources & evidence

ORD record
ord-af4ee9a92c7e4eacaa297af8b680033f
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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