N-bromobutanimide → HCID 67494671, compound

HRID 2047123Notes

Reaction equation

HRID 2047123 reaction equation
[CH3:1][Si:2]([CH3:49])([CH3:48])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:46])[CH3:45])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([CH:27]2[CH2:32][CH2:31][CH2:30][N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28]2)[CH:9]=1.C1C(=O)N([Br:57])C(=O)C1>CC#N>[CH3:47][Si:44]([CH3:46])([CH3:45])[CH2:43][CH2:42][O:41][CH2:40][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:48])[CH3:49])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([CH:27]2[CH2:32][CH2:31][CH2:30][N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28]2)[C:9]=1[Br:57]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67494798HCID 67494798, compound

Product 1

HCID 67494671HCID 67494671, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate (350 mg, 0.50 mmol) in CH3CN (5.0 mL) was added NBS (90 mg, 0.50 mmol). The mixture was stirred at it for 3 h and concentrated in vacuo. The residue was purified by Biotage (CH2Cl2/EtOAc, 100:1 to 10:1) to give the title compound as light yellow solid. LC/MS RT=2.49 min. Mass calculated for, M+H 768.29, observed 389.17.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by Biotage (CH2Cl2/EtOAc, 100:1 to 10:1)

Sources & evidence

ORD record
ord-2bb343ce3ccf4dba8eacbf22861422bd
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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