Chlorotrimethylsilane → HCID 44468025, compound

HRID 2381746Notes

Reaction equation

HRID 2381746 reaction equation
[CH2:1]([NH:8][C:9]1[C:10]2[C:18]([C:19]#[N:20])=[CH:17][N:16](S(C3C=CC(C)=CC=3)(=O)=O)[C:11]=2[N:12]=[C:13](Cl)[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:31][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[N:38]([CH3:42])[C:37](=[O:43])[CH2:36][CH2:35]2.C[Si](Cl)(C)C>C(O)CCC.O1CCOCC1>[CH2:1]([NH:8][C:9]1[C:10]2[C:18]([C:19]#[N:20])=[CH:17][NH:16][C:11]=2[N:12]=[C:13]([NH:31][C:32]2[CH:33]=[C:34]3[C:39](=[CH:40][CH:41]=2)[N:38]([CH3:42])[C:37](=[O:43])[CH2:36][CH2:35]3)[N:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 218777566-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-oneHCID 57990384HCID 57990384, compound

Product 1

HCID 44468025HCID 44468025, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-(benzylamino)-2-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (54 mg, 0.12 mmol), 6-amino-1-methyl-3,4-dihydroquinolin-2(1H)-one (43 mg, 0.24 mmol) and trimethylsilyl chloride (0.200 mL, 1.58 mmol) in nBuOH (2.5 mL) and dioxane (1.5 mL) was stirred at 116° C. for 20 h. It was concentrated in vacuo. The residue was purified by HPLC to give the titled compound. MS 424.3 (M+H); UV 207.7, 273.1 nm.

Workup

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

Sources & evidence

ORD record
ord-c5c33c7d5b2e474d986d32eb235ddd14
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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