Dimethylformamide → HCID 46174556, compound

HRID 2035617Notes

Reaction equation

HRID 2035617 reaction equation
Cl.Cl.[N:3]1[N:4]=[C:5]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[C:15]([O:22][CH2:23][C:24]4([F:30])[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)[CH:16]=[CH:17][CH:18]=3)[N:13]=2)[N:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12.CN(C=O)C.Br[CH2:37][C:38]([NH2:40])=[O:39]>C1COCC1.ClCCl.C([O-])(O)=O.[Na+].O>[N:3]1[N:4]=[C:5]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[C:15]([O:22][CH2:23][C:24]4([F:30])[CH2:29][CH2:28][N:27]([CH2:37][C:38]([NH2:40])=[O:39])[CH2:26][CH2:25]4)[CH:16]=[CH:17][CH:18]=3)[N:13]=2)[N:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12

Participants

8

Reactant 3

HCID 6228DimethylformamideHCID 696322-BromoacetamideHCID 67231295HCID 67231295, compound

Product 1

HCID 46174556HCID 46174556, compoundYield 29%

Reagents, catalysts & solvents 4

HCID 516892Sodium BicarbonateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of 2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-((4-fluoropiperidin-4-yl)methoxy)quinoline dihydrochloride (0.050 g, 0.111 mmol) and TEA (0.0619 mL, 0.444 mmol) in 0.4 mL THF, 0.3 mL dichloromethane, and 0.2 mL DMF was added 2-bromoacetamide (0.0184 g, 0.133 mmol). The reaction mixture was heated in a 40° C. reaction block and stirred 1 hour. The reaction mixture was cooled to ambient temperature, several drops of saturated NaHCO3 were added, and the milky mixture was heated back to 40° C. and stirred another 3 hours. The reaction mixture was cooled to ambient temperature, diluted with water, and the resulting solids were collected by vacuum filtration through a 0.2 micron nylon filter disc, rinsed with water, air dried, then washed successively with ethyl acetate, dichloromethane, and ether, air dried, and dried in vacuo to give the title compound (0.014 g, 0.0322 mmol, 29.0% yield) as a white powder. MS APCI (+) m/z 435 (M+1) detected.

Workup

  1. customreaction block
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. temperaturethe milky mixture was heated back to 40° C.
  4. stirringstirred another 3 hours
  5. temperatureThe reaction mixture was cooled to ambient temperature
  6. filtrationthe resulting solids were collected by vacuum filtration through a 0.2 micron nylon
  7. filtrationfilter disc
  8. washrinsed with water, air
  9. customdried
  10. washwashed successively with ethyl acetate, dichloromethane, and ether, air
  11. customdried
  12. customdried in vacuo

Sources & evidence

ORD record
ord-ec5356ee1548498482d1f008e9200536
Source dataset
uspto-grants-2013_11
Patent number
US08575145B2

Reaction notes

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