Triethylamine → HCID 59507012, compound

HRID 1800443Notes

Reaction equation

HRID 1800443 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[S:7][C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[C:10]([O:15][C:16]1[CH:17]=[C:18]([NH:23][C:24](=[O:35])[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=3)[CH:19]=[CH:20][C:21]=1[CH3:22])[N:9]=2)=[O:4].C(N(CC)CC)C.[CH3:43][N:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:22][C:21]1[CH:20]=[CH:19][C:18]([NH:23][C:24](=[O:35])[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:33])([F:32])[F:34])[CH:26]=2)=[CH:17][C:16]=1[O:15][C:10]1[N:9]=[C:8]2[S:7][C:6]([NH:5][C:3](=[O:4])[CH2:2][N:47]3[CH2:48][CH2:49][N:44]([CH3:43])[CH2:45][CH2:46]3)=[N:14][C:13]2=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 86645996HCID 86645996, compound

Product 1

HCID 59507012HCID 59507012, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-[3-({2-[(chloroacetyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methylphenyl]-3-(trifluoromethyl)benzamide (218 mg, 0.419 mmol) in tetrahydrofuran (5 mL) were added triethylamine (117 μL, 0.838 mmol) and 1-methylpiperazine (93.4 μL, 0.838 mmol), and the mixture was stirred at 60° C. for 14 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to basic silica gel column chromatography (ethyl acetate/methanol=100/0→90/10), and precipitated with ethyl acetate to give the title compound (134 mg, 55%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. customThe solvent was evaporated under reduced pressure
  6. customprecipitated with ethyl acetate

Sources & evidence

ORD record
ord-db666d6d95af459e972d90ae46e5f49b
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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