Chlorotrimethylsilane → HCID 57990318, compound

HRID 2281375Notes

Reaction equation

HRID 2281375 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:21]2[CH2:26][CH2:25][CH:24]([CH2:27][NH:28]C(=O)OC(C)(C)C)[CH2:23][CH2:22]2)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1.[NH2:36][C:37]1[CH:42]=[CH:41][C:40]([N:43]2[CH2:48][CH2:47][N:46]([C:49](=[O:51])[CH3:50])[CH2:45][CH2:44]2)=[CH:39][CH:38]=1.C[Si](Cl)(C)C>CCCCO>[NH2:28][CH2:27][CH:24]1[CH2:25][CH2:26][N:21]([C:4]2[C:5]3[CH:10]=[CH:9][N:8]([S:11]([C:14]4[CH:15]=[CH:16][C:17]([CH3:18])=[CH:19][CH:20]=4)(=[O:13])=[O:12])[C:6]=3[N:7]=[C:2]([NH:36][C:37]3[CH:38]=[CH:39][C:40]([N:43]4[CH2:44][CH2:45][N:46]([C:49](=[O:51])[CH3:50])[CH2:47][CH2:48]4)=[CH:41][CH:42]=3)[N:3]=2)[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-oneHCID 57990418HCID 57990418, compound

Product 1

HCID 57990318HCID 57990318, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

A mixture of tert-butyl (1-(2-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-yl)methylcarbamate (303 mg, 0.583 mmol), 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (191 mg, 0.872 mmol) and trimethylsilyl chloride (0.400 mL, 3.16 mmol) in n-BuOH (6 mL) was stirred at 135° C. for 40 h. n-BuOH was removed in vacuo. The residue was purified by HPLC to give 1-(4-(4-(4-(4-(aminomethyl)piperidin-1-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (60 mg).

Workup

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

Sources & evidence

ORD record
ord-591620ffc197440aa19db4aada571752
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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