N1-(3-Fluoro-4-(2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N3-(2-methoxyphenyl)malonamide → HCID 178489596, compound

HRID 418630Notes

Reaction equation

HRID 418630 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:31][C:32](=[O:45])[CH2:33][C:34]([NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[O:43][CH3:44])=[O:35])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[N:19]=[CH:20][N:21](COCC[Si](C)(C)C)[CH:22]=3)[S:17][C:10]=12>C(O)(C(F)(F)F)=O>[NH:21]1[CH:22]=[C:18]([C:16]2[S:17][C:10]3[C:11](=[N:12][CH:13]=[CH:14][C:9]=3[O:8][C:7]3[CH:6]=[CH:5][C:4]([NH:31][C:32](=[O:45])[CH2:33][C:34]([NH:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[O:43][CH3:44])=[O:35])=[CH:3][C:2]=3[F:1])[CH:15]=2)[N:19]=[CH:20]1

Participants

3

Reactant 1

HCID 58790420N1-(3-Fluoro-4-(2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N3-(2-methoxyphenyl)malonamide

Product 1

HCID 178489596HCID 178489596, compoundYield 113.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 105 (42 mg, 0.0648 mmol) in TFA (1 ml) was stirred at RT for 30 mins. The TFA was removed by evaporation and then 4N HCl in dioxane (0.5 ml) was added and the mixture was concentrated to dryness. The residual solid was triturated with diethyl ether to afford title compound 102 (38 mg, 100% yield). MS (m/z): 518.1 (M+H).

Workup

  1. customThe TFA was removed by evaporation
  2. addition4N HCl in dioxane (0.5 ml) was added
  3. concentrationthe mixture was concentrated to dryness
  4. customThe residual solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-bebcbbd8c23f4e46a8b5e55a54acf9c0
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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