Methylamine → HCID 178485306, compound

HRID 1023863Notes

Reaction equation

HRID 1023863 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=2[O:8][CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([O:15]C)=O)[N:3]=[CH:2]1.[CH3:25][NH2:26]>CO>[NH:1]1[CH:5]=[C:4]([C:6]2[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=2[O:8][CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([NH:26][CH3:25])=[O:15])[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 178497628HCID 178497628, compound

Product 1

HCID 178485306HCID 178485306, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 2-(2-(2-(1H-imidazol-4-yl)phenoxy)ethyl)benzoate (30 mg, 0.093 mmol) and methylamine (2M, 3.3 mL, 6.51 mmol) in methanol was heated at 70° C. for 7 days. Methanol was removed under reduced pressure the crude product was purified by flash column chromatography to afford the desired product as a yellow solid (11 mg, 0.034 mmol, 37%). 1H NMR (CD3OD): 2.69 (s, 3H), 3.29 (t, 2H, J=6.4 Hz), 4.36 (t, 2H, J=6.4 Hz), 6.96 (dt, 1H, J=7.6 Hz, 1.2 Hz), 7.04 (d, 1H, J=8 Hz), 7.17-7.41 (m, 6H), 7.63 (s, 1H), 7.76 (s, 1H).

Workup

  1. customMethanol was removed under reduced pressure the crude product
  2. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-66f07e9730864d68bf3523ba22512c27
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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