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 2193697Notes

Reaction equation

HRID 2193697 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-df5c2713c1a84aeca2e23e8181471af1
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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