4-Methoxybenzylamine → HCID 25120845, compound

HRID 2280939Notes

Reaction equation

HRID 2280939 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([N:12]([CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH:21]3[CH2:23][CH2:22]3)[CH2:16][CH2:15]2)[CH3:13])=[O:11])[C:5]([CH3:24])=[CH:4][N:3]=1.[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH2:32])=[CH:29][CH:28]=1.C(N(C(C)C)CC)(C)C>C(O)CCC>[CH:21]1([CH2:20][N:17]2[CH2:18][CH2:19][CH:14]([N:12]([CH3:13])[C:10](=[O:11])[CH2:9][NH:8][C:6]3[C:5]([CH3:24])=[CH:4][N:3]=[C:2]([NH:32][CH2:31][C:30]4[CH:33]=[CH:34][C:27]([O:26][CH3:25])=[CH:28][CH:29]=4)[N:7]=3)[CH2:15][CH2:16]2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 754524-MethoxybenzylamineHCID 81531DiisopropylethylamineHCID 59336103HCID 59336103, compound

Product 1

HCID 25120845HCID 25120845, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of Compound 106 (93 mg), 4-methoxybenzylamine (345 μL) and diisopropylethylamine (45.5 μL) in n-butanol (1.5 mL) was stirred overnight under reflux. Subsequently, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (methylene chloride:methanol=50:1 to 4:1) to give 43 mg (36% yield) of the desired product as a white amorphous.

Workup

  1. temperatureunder reflux
  2. concentrationSubsequently, the reaction mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (methylene chloride:methanol=50:1 to 4:1)

Sources & evidence

ORD record
ord-87631d4b88604854baabf1989651b9a3
Source dataset
uspto-grants-2015_09
Patent number
US09139559B2

Reaction notes

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