2-Pyridinemethanamine → HCID 22980443, compound

HRID 1861816Notes

Reaction equation

HRID 1861816 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.O.O[N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=N1.NCC1C=CC=CN=1>CN(C=O)C>[N:18]1[CH:19]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:20][NH:16][C:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[N:7][CH:6]=2)[N:1]=1)=[O:13]

Participants

5

Reactant 3

HCID 195092-PyridinemethanamineHCID 7359081,6-Naphthyridine-2-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 22980443HCID 22980443, compoundYield 103.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring mixture of 2-[1,6]naphthyridinecarboxylic acid (50 mg, 0.287 mmol) in anhydrous DMF (1.0 mL) at room temperature was added sequentially 1-hydroxybenzotriazole hydrate (42.7 mg, 0.316 mmol), 2-(aminomethyl)pyridine (45.3 μL, 0.431 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarboiimide hydrochloride (61.8 mg, 0.316 mmol). The resulting mixture was allowed to stir at room temperature overnight and it was found to be clear. The solvent was removed under vacuum. Flash column chromatography of the residue (50% hexane/ethyl acetate to 5% methanol/ethyl acetate) afforded the desired product as a light brown solid (78.7 mg, 99%): m.p. 123-125° C.

Workup

  1. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-84d01925f5bc495aaa0f1330afe1dd1a
Source dataset
uspto-grants-2003_03
Patent number
US06534520B2

Reaction notes

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