N-bromobutanimide → HCID 69929544, compound

HRID 1913221Notes

Reaction equation

HRID 1913221 reaction equation
[CH3:1][Si:2]([CH3:50])([CH3:49])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH2:29][CH:30]2[CH2:35][CH2:34][CH:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:32][CH2:31]2)[CH:9]=1.[Br:51]N1C(=O)CCC1=O>C(#N)C>[CH3:46][Si:45]([CH3:48])([CH3:47])[CH2:44][CH2:43][O:42][CH2:41][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:49])[CH3:50])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH2:29][CH:30]2[CH2:35][CH2:34][CH:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:32][CH2:31]2)[C:9]=1[Br:51]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66897145HCID 66897145, compound

Product 1

HCID 69929544HCID 69929544, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 20 mL scintillation vial was charged ethyl 4-((7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)cyclohexanecarboxylate (Int-4l, 265 mg, 0.37 mmol) and N-bromosuccinimide (80 mg, 0.45 mmol). To this was added acetonitrile (5 mL). The resulting solution was stirred at room temperature for 18 hours. At 18 hours, the reaction was reduced in vacuo and the residue was purified via silica gel chromatography to yield the title compound as yellow oil. Yield=255 mg.

Workup

  1. waitAt 18 hours
  2. customthe residue was purified via silica gel chromatography

Sources & evidence

ORD record
ord-7464b224e51042569c744073e7892228
Source dataset
uspto-grants-2013_12
Patent number
US08609675B2

Reaction notes

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