2-Amino-3-cyanopyridine → N-(3-cyano-pyridin-2-yl)-2-phenethyloxy-acetamide

HRID 2100468Notes

Reaction equation

HRID 2100468 reaction equation
[CH2:1]([O:9][CH2:10][C:11](Cl)=[O:12])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH2:14][C:15]1[C:20]([C:21]#[N:22])=[CH:19][CH:18]=[CH:17][N:16]=1>CN(C1C=CN=CC=1)C.ClCCl.N1C=CC=CC=1>[C:21]([C:20]1[C:15]([NH:14][C:11](=[O:12])[CH2:10][O:9][CH2:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[N:16][CH:17]=[CH:18][CH:19]=1)#[N:22]

Participants

6

Reactant 2

HCID 8182592-Amino-3-cyanopyridineHCID 19593432Phenethyloxy-acetyl chloride

Product 1

HCID 68568667N-(3-cyano-pyridin-2-yl)-2-phenethyloxy-acetamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Phenethyloxy-acetyl chloride (3.79 g, 6.12 mmol) was added to a solution of 2-amino-3-cyanopyridine ([24517-64-4], 662 mg, 5.56 mmol) and DMAP (67 mg, 0.55 mmol) in a mixture of dichloromethane (8 ml) and pyridine (8 ml). After 3 h at r.t., the solvent was evaporated, and N-(3-cyano-pyridin-2-yl)-2-phenethyloxy-acetamide was isolated from the residue by column chromatography (silica gel, heptane, ethyl acetate, methanol). MS: m/e=282.1 [M+H+], 1H NMR (d6-DMSO): 2.91 (t, 2H), 3.77 (t, 2H), 4.18 (s, 2H), 7.17-7.23 (m, 5H), 7.47 (dd, 1H), 8.37 (d, 1H), 8.71 (d, 1H), 10.55 (bs, 1H).

Workup

  1. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8d16e9db08e84dd09c986db46a983e44
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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