Trimethylsilyl iodide → HCID 59134035, compound

HRID 1994411Notes

Reaction equation

HRID 1994411 reaction equation
I[Si](C)(C)C.[Cl:6][C:7]1[CH:58]=[CH:57][C:10]([CH2:11][CH:12]2[N:17]3[C:18](=[O:52])[CH:19]([NH:33][C:34]([CH:36]4[CH2:41][CH2:40][N:39](C(OCC5C=CC=CC=5)=O)[CH2:38][CH2:37]4)=[O:35])[CH2:20][N:21]([S:22]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=4[Cl:32])(=[O:24])=[O:23])[CH:16]3[CH2:15][N:14]([CH:53]([CH3:55])[CH3:54])[C:13]2=[O:56])=[CH:9][CH:8]=1>C(#N)C>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][CH:12]2[N:17]3[C:18](=[O:52])[CH:19]([NH:33][C:34]([CH:36]4[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]4)=[O:35])[CH2:20][N:21]([S:22]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=4[Cl:32])(=[O:24])=[O:23])[CH:16]3[CH2:15][N:14]([CH:53]([CH3:55])[CH3:54])[C:13]2=[O:56])=[CH:57][CH:58]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 68693749HCID 68693749, compound

Product 1

HCID 59134035HCID 59134035, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

103 mg (0.517 mmol) of iodotrimethylsilane were added to a solution of 104 mg (0.129 mmol) of benzyl 4-[6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropyl-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-ylcarbamoyl]piperidine-1-carboxylate in 2.5 ml of acetonitrile at room temperature with stirring. After 2 hours, the mixture was concentrated. The residue was purified on a Varian Bond-Elut SCX ion exchange cartridge (elution with methanol, then with 3N—NH3 in methanol). The purified amine was converted into the hydrochloride salt. 75 mg of the desired compound were obtained. LC/MS (expected monoisotopic MW=669.13; measured value (M+H)=670)

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was purified on a Varian Bond-Elut SCX ion exchange cartridge (
  3. washelution with methanol

Sources & evidence

ORD record
ord-d22e67cbe53f48049e60cc2d67e7e88f
Source dataset
uspto-grants-2010_01
Patent number
US07652007B2

Reaction notes

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