Methylamine → Methyl 2-(4-((methylamino)methyl)phenyl)benzo[d]oxazole-7-carboxylate

HRID 415204Notes

Reaction equation

HRID 415204 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1.[CH3:22][NH2:23]>CO>[CH3:22][NH:23][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 66621208Methyl 2-(4-(bromomethyl)phenyl)benzo[d]oxazole-7-carboxylate

Product 1

HCID 66621355Methyl 2-(4-((methylamino)methyl)phenyl)benzo[d]oxazole-7-carboxylateYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of methyl 2-(4-(bromomethyl)phenyl)benzo[d]oxazole-7-carboxylate (500 mg, 1.4 mmol in methanol (10 mL), was added methylamine solution (4 mL), and the resulting mixture was stirred at room temperature for 1 hr, then heated to 30° C. for 30 min. Then the solvent was evaporated and purified by pre-HPLC to obtain methyl 2-(4-((methylamino)methyl)phenyl)benzo[d]oxazole-7-carboxylate (as TFA salt, 90 mg, yield 42%). LC-MS (ESI) m/z 297 [M+1]+.

Workup

  1. temperatureheated to 30° C. for 30 min
  2. customThen the solvent was evaporated
  3. custompurified by pre-HPLC

Sources & evidence

ORD record
ord-236db4d6da60448a9d0946d239f1f8eb
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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