Chlorotrimethylsilane → HCID 57990284, compound

HRID 2281378Notes

Reaction equation

HRID 2281378 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:21]2[CH2:25][CH2:24][C@H:23]([OH:26])[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.[NH2:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH2:39][CH2:38][N:37]([C:40](=[O:42])[CH3:41])[CH2:36][CH2:35]2)=[CH:30][CH:29]=1.C[Si](Cl)(C)C>CCCCO>[OH:26][C@H:23]1[CH2:24][CH2:25][N:21]([C:4]2[C:5]3[CH:10]=[CH:9][N:8]([S:11]([C:14]4[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=4)(=[O:13])=[O:12])[C:6]=3[N:7]=[C:2]([NH:27][C:28]3[CH:29]=[CH:30][C:31]([N:34]4[CH2:35][CH2:36][N:37]([C:40](=[O:42])[CH3:41])[CH2:38][CH2:39]4)=[CH:32][CH:33]=3)[N:3]=2)[CH2:22]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-oneHCID 57990281HCID 57990281, compound

Product 1

HCID 57990284HCID 57990284, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

A mixture of (S)-1-(2-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-ol (201 mg, 0.512 mmol), 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (160 mg, 0.730 mmol) and trimethylsilyl chloride (0.200 mL, 1.58 mmol) in n-BuOH (5 mL) was stirred at 120° C. for 40 h. n-BuOH was removed in vacuo. The residue was purified by HPLC to give (S)-1-(4-(4-(4-(3-hydroxypyrrolidin-1-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (80 mg). MS 576.5 (M+H)

Workup

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

Sources & evidence

ORD record
ord-e58417e08daf4d39b6849e7529edba1b
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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