2-Pyridinemethanamine → HCID 70664876, compound

HRID 1403628Notes

Reaction equation

HRID 1403628 reaction equation
Cl[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.CCN(C(C)C)C(C)C.[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:38][NH2:39]>CS(C)=O>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:3]2[C:2]([NH:39][CH2:38][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=3)=[N:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=3)[N:4]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 195092-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 77231184Methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate

Product 1

HCID 70664876HCID 70664876, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (200 mg, 0.95 mmol) in DMSO (5 mL) was added DIEA (245 mg, 1.90 mmol) and pyridin-2-ylmethanamine (124 mg, 1.15 mmol), and the reaction was stirred overnight at 90° C. in an oil bath. The solids were precipitated from water (50 mL), collected by filtration, washed with AcOEt (10 mL), and dried to afford methyl 2-(4-fluorophenyl)-3-[(pyridin-2-ylmethyl)amino]quinoxaline-6-carboxylate as a yellow solid (200 mg, 81%).

Workup

  1. customThe solids were precipitated from water (50 mL)
  2. filtrationcollected by filtration
  3. washwashed with AcOEt (10 mL)
  4. customdried

Sources & evidence

ORD record
ord-50c784886004450d925acf166b3307ec
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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