Chlorotrimethylsilane → HCID 178473884, compound

HRID 2381609Notes

Reaction equation

HRID 2381609 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][NH:18]C(=O)OC(C)(C)C)[CH2:13][CH2:12]2)[N:3]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][N:36]([C:39](=[O:41])[CH3:40])[CH2:35][CH2:34]2)=[CH:29][CH:28]=1.C[Si](Cl)(C)C>CCCCO>[NH2:18][CH2:17][CH:14]1[CH2:13][CH2:12][N:11]([C:4]2[N:3]=[C:2]([NH:26][C:27]3[CH:28]=[CH:29][C:30]([N:33]4[CH2:34][CH2:35][N:36]([C:39](=[O:41])[CH3:40])[CH2:37][CH2:38]4)=[CH:31][CH:32]=3)[N:10]=[C:9]3[C:5]=2[N:6]=[CH:7][NH:8]3)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-oneHCID 178453095HCID 178453095, compound

Product 1

HCID 178473884HCID 178473884, compoundYield 9.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

A mixture of tert-butyl (1-(2-chloro-9H-purin-6-yl)piperidin-4-yl)methylcarbamate (100 mg, 0.272 mmol), 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (120 mg, 0.548 mmol) and trimethylsilyl chloride (0.300 mL, 2.37 mmol) in n-BuOH (4 mL) was stirred at 135° C. for 70 h. n-BuOH was removed in vacuo. The residue was purified by HPLC to give the titled compound (12 mg). MS 450.6 (M+H); UV 200.0, 270.8 nm.

Workup

  1. customwas removed in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-3fb4881750fd494680362cd60c7c9dc2
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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