Picolinic acid → Pyridine-2-carboxylic acid 4-hydroxymethyl-benzylamide

HRID 970940Notes

Reaction equation

HRID 970940 reaction equation
[NH2:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17](O)=[O:18].ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[OH:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([CH2:2][NH:1][C:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=2)=[O:18])=[CH:4][CH:5]=1

Participants

7

Reactant 5

HCID 1018Picolinic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6496943[4-(Aminomethyl)phenyl]methanol

Product 1

HCID 22601292Pyridine-2-carboxylic acid 4-hydroxymethyl-benzylamideYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using General Procedure F: To a stirred solution of 4-aminomethylbenzyl alcohol (203 mg, 1.48 mmol) in DMF (3 mL) was added picolinic acid (198 mg, 1.61 mmol), 1-hydroxybenzotriazole (213 mg, 1.58 mmol), N,N-diisopropylethylamine (0.39 mL, 2.24 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide HCl (EDC) (315 mg, 1.64 mmol) and the mixture stirred overnight at room temperature. Standard work-up afforded the title compound (340 mg, 95%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 4.67 (d, 2H, J=6.0 Hz), 4.69 (s, 2H), 7.36 (br s, 4H), 7.43-7.44 (m, 1H), 7.85-7.86 (m, 1H), 8.24 (d, 1H, J=9.0 Hz), 8.52 (br s, 1H), 8.52 (d, 1H, J=3.0 Hz). ES-MS m/z 243 (M+H).

Sources & evidence

ORD record
ord-d31189298b614c27bd5180ff456da0a3
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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