Chlorotrimethylsilane → HCID 44467606, compound

HRID 2381608Notes

Reaction equation

HRID 2381608 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][CH:26]([CH2:29][NH:30]C(=O)OC(C)(C)C)[CH2:25][CH2:24]2)[C:5]2[C:10]([C:11]#[N:12])=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:6]=2[N:7]=1.[NH2:38][C:39]1[CH:44]=[CH:43][C:42]([N:45]2[CH2:50][CH2:49][N:48]([C:51](=[O:53])[CH3:52])[CH2:47][CH2:46]2)=[CH:41][CH:40]=1.C[Si](Cl)(C)C>CCCCO>[C:51]([N:48]1[CH2:47][CH2:46][N:45]([C:42]2[CH:43]=[CH:44][C:39]([NH:38][C:2]3[N:3]=[C:4]([N:23]4[CH2:24][CH2:25][CH:26]([CH2:29][NH2:30])[CH2:27][CH2:28]4)[C:5]4[C:10]([C:11]#[N:12])=[CH:9][NH:8][C:6]=4[N:7]=3)=[CH:40][CH:41]=2)[CH2:50][CH2:49]1)(=[O:53])[CH3:52]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-oneHCID 57990336HCID 57990336, compound

Product 1

HCID 44467606HCID 44467606, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

A mixture of tert-butyl (1-(2-chloro-5-cyano-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-yl)methylcarbamate (180 mg, 0.330 mmol), 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (137 mg, 0.625 mmol) and trimethylsilyl chloride (0.300 mL, 2.37 mmol) in n-BuOH (5 mL) was stirred at 135° C. for 40 h. n-BuOH was removed in vacuo. The residue was purified by HPLC to give the titled compound (25 mg). MS 474.5 (M+H); UV 200.8, 277.8 nm.

Workup

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

Sources & evidence

ORD record
ord-a5572fdfb58f42918bf93c31a8dc746e
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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