Triethylamine → N-(2-Pyridylmethyl)-4-[2-(2-benzyloxy-3-pyridyl)ethyl]benzamide

HRID 2395072Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14]([CH2:15][CH2:16][C:17]2[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=2)=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C=O)C>[N:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[CH2:27][NH:26][C:21](=[O:22])[C:20]1[CH:19]=[CH:18][C:17]([CH2:16][CH2:15][C:14]2[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-[2-(2-benzyloxy-3-pyridyl)ethyl]benzoic acid (0.48 g, 1.44 mmol) and 2-aminomethylpyridine (0.189 g, 1.748 mmol) were dissolved in DMF (20 ml) and cooled to 0° C. Triethylamine (0.15 g, 1.5 mmol) was added followed by diphenylphosphorylazide (0.41 g, 1.48 mmol). The reaction mixture was stirred under argon and allowed to warm to ambient temperature overnight. The reaction was partitioned between EtOAc/water, the organic phase was washed with aqueous sodium bicarbonate, water, dried (MgSO4) and evaporated. The residue was purified by flash chromatography (MeOH/CH2Cl2) followed by recrystallisation from EtOAc/hexane and then from EtOH/water to give the title product.

Workup

temperatureto warm to ambient temperature overnight
customThe reaction was partitioned between EtOAc/water
washthe organic phase was washed with aqueous sodium bicarbonate, water
dry with materialdried (MgSO4)
customevaporated
customThe residue was purified by flash chromatography (MeOH/CH2Cl2)
customfollowed by recrystallisation from EtOAc/hexane

Sources & evidence

ORD record: ord-e771f3f386ff4f268896a13d963552a4
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05811459

Reaction notes

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