Diethylamine → HCID 68994690, compound

HRID 1988000Notes

Reaction equation

HRID 1988000 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]2[C:6](=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:10][CH:11]=2)[N:7]=1.[CH2:16]([NH:18][CH2:19][CH3:20])[CH3:17]>C1COCC1>[CH2:16]([N:18]([CH2:2][C:3]1[O:4][C:5]2[C:6](=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:10][CH:11]=2)[N:7]=1)[CH2:19][CH3:20])[CH3:17]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 689963151006601-77-9

Product 1

HCID 68994690HCID 68994690, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-(chloromethyl)benzoxazole-4-carboxylate (267 mg, 1.18 mmol) and diethylamine (2.0 mL, 27.4 mmol) in THF (15 mL) was stirred at ambient temperature overnight The solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, 10:1:0.1 dichloromethane/methanol/concentrated ammonium hydroxide), followed by purification by preparative TLC (silica gel, 10:1:0.1 dichloromethane/methanol/concentrated ammonium hydroxide) to afford methyl 2-(diethylaminomethyl)benzoxazole-4-carboxylate (200 mg, 64%) as a yellow oil: 1H NMR (300 MHz, CDCl3) δ 7.99 (dd, J=9.0, 1.0 Hz, 1H), 7.74 (dd, J=9.0, 1.0 (1H), 6.40 (t, J=8.1 Hz, 1H), 4.09 (s, 2H), 4.04 (s, 3H), 2.74-2.69 (m, 4H), 1.13 (t, J=6.6 Hz, 1H); MS (ESI+) m/z 263 (M+H).

Workup

  1. customwas removed under reduced pressure
  2. customthe residue was purified by column chromatography (silica gel, 10:1:0.1 dichloromethane/methanol/concentrated ammonium hydroxide)
  3. customfollowed by purification by preparative TLC (silica gel, 10:1:0.1 dichloromethane/methanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-3429af927b5e4f2a8936a464a8296cc1
Source dataset
uspto-grants-2009_06
Patent number
US07553846B2

Reaction notes

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