N-Iodosuccinimide → HCID 66584876, compound

HRID 2369002Notes

Reaction equation

HRID 2369002 reaction equation
[CH3:1][Si:2]([CH3:42])([CH3:41])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:8]1[N:13]2[N:14]=[CH:15][CH:16]=[C:12]2[N:11]=[C:10]([CH:17]2[CH2:24][CH:23]3[N:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:19]([CH2:20][O:21][CH2:22]3)[CH2:18]2)[CH:9]=1.C1C(=O)N([I:50])C(=O)C1>C(#N)C>[CH3:40][Si:37]([CH3:39])([CH3:38])[CH2:36][CH2:35][O:34][CH2:33][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:41])[CH3:42])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([I:50])=[C:12]2[N:11]=[C:10]([CH:17]2[CH2:18][CH:19]3[N:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:23]([CH2:22][O:21][CH2:20]3)[CH2:24]2)[CH:9]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 67294552HCID 67294552, compound

Product 1

HCID 66584876HCID 66584876, compoundYield 103.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-butyl 7-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate (1.1 g, 1.77 mmol) was suspended in acetonitrile (20 mL) and treated with NIS (396.4 mg, 1.77 mmol) at room temperature. The mixture was stirred for 30 min. Then solvent was evaporated off under reduced pressure, and the crude material was purified by column chromatography (SiO2, 0-40% hexane-EtOAc) to provide desired compound tert-butyl 7-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate (1.37 g). HPLC-MS tR=3.37 min (UV254 nm). Mass calculated for formula C30H52IN5O5Si2 745.2; observed MH+ (LCMS) 746.0 (m/z).

Workup

  1. customThen solvent was evaporated off under reduced pressure
  2. customthe crude material was purified by column chromatography (SiO2, 0-40% hexane-EtOAc)

Sources & evidence

ORD record
ord-b2ef23d701da4be2a6e130d6249a6a9b
Source dataset
uspto-grants-2014_04
Patent number
US08703784B2

Reaction notes

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