Chlorotrimethylsilane → HCID 57990350, compound

HRID 2381641Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([NH:27][CH2:28][CH:29]2[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]2)[C:5]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:6]=2[N:7]=1.[NH2:42][C:43]1[CH:48]=[CH:47][C:46]([N:49]2[CH2:54][CH2:53][N:52]([C:55](=[O:57])[CH3:56])[CH2:51][CH2:50]2)=[CH:45][CH:44]=1.C[Si](Cl)(C)C>C(O)CCC>[NH:32]1[CH2:33][CH2:34][CH:29]([CH2:28][NH:27][C:4]2[C:5]3[C:10]([C:11]4[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=4)=[CH:9][NH:8][C:6]=3[N:7]=[C:2]([NH:42][C:43]3[CH:44]=[CH:45][C:46]([N:49]4[CH2:50][CH2:51][N:52]([C:55](=[O:57])[CH3:56])[CH2:53][CH2:54]4)=[CH:47][CH:48]=3)[N:3]=2)[CH2:30][CH2:31]1

Participants

Conditions

Temperature: 135 °C

Procedure

A mixture of tert-butyl 4-((2-chloro-5-(pyridine-4-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)methyl)piperidine-1-carboxylate (90 mg, 0.15 mmol), 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (66 mg, 0.30 mmol) and TMSCl (0.100 mL, 0.79 mmol) in nBuOH (4 mL) was stirred at 135° C. for 68 h. It was then concentrated in vacuo. The residue was purified by HPLC to give the titled compound (26 mg). MS 526.47 (M+H); UV 202.6, 259.2, 304.3 nm.

Workup

concentrationIt was then concentrated in vacuo
customThe residue was purified by HPLC

Sources & evidence

ORD record: ord-21191e53b56847689640528d3bd9beca
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258144B2

Reaction notes

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