N,N-Dimethylethylenediamine → Methyl 2-(3-((2-(dimethylamino)ethylamino)methyl)phenyl)benzo[d]oxazole-7-carboxylate

HRID 415224Notes

Reaction equation

HRID 415224 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1.[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH2:26]>C(O)C>[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH:26][CH2:2][C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 66620978Methyl 2-(3-(bromomethyl)phenyl)benzo[d]oxazole-7-carboxylate

Product 1

HCID 66621124Methyl 2-(3-((2-(dimethylamino)ethylamino)methyl)phenyl)benzo[d]oxazole-7-carboxylateYield 141.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2-(3-(bromomethyl)phenyl)benzo[d]oxazole-7-carboxylate (70 mg, 0.2 mmol) and N,N-dimethylethane-1,2-diamine (140.8 mg, 1.6 mmol) were added to ethanol (30 mL) and the mixture was stirred at room temperature for 1 hr and evaporated under reduced pressure to obtain methyl 2-(3-((2-(dimethylamino)ethylamino)methyl)phenyl)benzo[d]oxazole-7-carboxylate (100 mg, yield 85%). LC-MS (ESI) m/z 354 [M+1]+.

Workup

  1. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-791b2d5a5422438d8644c6c33a0f75d4
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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