N-Iodosuccinimide → HCID 67494276, compound

HRID 2047008Notes

Reaction equation

HRID 2047008 reaction equation
[I:1]N1C(=O)CCC1=O.[CH3:9][Si:10]([CH3:54])([CH3:53])[CH2:11][CH2:12][O:13][CH2:14][N:15]([CH2:45][O:46][CH2:47][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])[C:16]1[N:21]2[N:22]=[CH:23][CH:24]=[C:20]2[N:19]=[C:18]([CH:25]2[CH2:30][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:28]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:27][CH2:26]2)[CH:17]=1>C(#N)C>[CH3:52][Si:49]([CH3:50])([CH3:51])[CH2:48][CH2:47][O:46][CH2:45][N:15]([CH2:14][O:13][CH2:12][CH2:11][Si:10]([CH3:9])([CH3:53])[CH3:54])[C:16]1[N:21]2[N:22]=[CH:23][C:24]([I:1])=[C:20]2[N:19]=[C:18]([CH:25]2[CH2:30][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:28]([C:38]([O:40][C:41]([CH3:43])([CH3:44])[CH3:42])=[O:39])[CH2:27][CH2:26]2)[CH:17]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 67494273HCID 67494273, compound

Product 1

HCID 67494276HCID 67494276, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Iodosuccinimide (1.26 g, 5.61 mmol, dissolved in 25 ml acetonitrile) was added into a solution of di-tert-butyl 5-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1,2-dicarboxylate (3.8 g, 5.61 mmol) in acetonitrile (26 mL). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated in vacuo and purified via silica gel chromatography (0% to 30% ethyl acetate in hexanes gradient) to yield the title compound (3.16 g, 70% yield) at clear oil. LC-MS: 804 [M+H].

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified via silica gel chromatography (0% to 30% ethyl acetate in hexanes gradient)

Sources & evidence

ORD record
ord-3b2c1edd314f46f7b29a3489603edffc
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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