Chlorotrimethylsilane → HCID 44468022, compound

HRID 2281513Notes

Reaction equation

HRID 2281513 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=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.[NH2:35][C:36]1[CH:37]=[C:38]2[C:43](=[CH:44][CH:45]=1)[N:42]([CH3:46])[C:41](=[O:47])[CH2:40][CH2:39]2.C[Si](Cl)(C)C>C(O)CCC>[F:34][C:31]1[CH:30]=[CH:29][C: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:35][C:36]3[CH:37]=[C:38]4[C:43](=[CH:44][CH:45]=3)[N:42]([CH3:46])[C:41](=[O:47])[CH2:40][CH2:39]4)[N:3]=2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 218777566-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-oneHCID 57990442HCID 57990442, compound

Product 1

HCID 44468022HCID 44468022, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 2-chloro-N-(4-fluorophenyl)-5-(pyridin-4-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (31 mg, 0.062 mmol), 6-amino-1-methyl-3,4-dihydroquinolin-2(1H)-one (25 mg, 0.14 mmol) and trimethylsilyl chloride (0.100 mL, 0.790 mmol) in nBuOH (1 mL) was stirred at 135° C. for 20 h. It was concentrated in vacuo. The residue was purified by HPLC to give the titled compound. MS 480.5 (M+H); UV 204.7, 281.7, 314.3 nm.

Workup

  1. concentrationIt was concentrated in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-eba180eefbb046e3882a29551f501e22
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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