2-Pyridinemethanamine → HCID 22980443, compound

HRID 1383416Notes

Reaction equation

HRID 1383416 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:12].O.ON1C2C=CC=C[C:19]=2N=N1.[NH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1>CN(C=O)C>[CH2:3]([CH2:2][C:11]([O:13][CH3:19])=[O:12])[CH3:4].[N:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH2:26][NH:25][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

6

Reactant 3

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

Product 2

HCID 12180Methyl butyrateYield 5%HCID 22980443HCID 22980443, compoundYield 207.5%

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 5 vacuum. Flash column chromatography of the residue (50% hexane/ethyl acetate to 5% methanol I 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 5 vacuum

Sources & evidence

ORD record
ord-6e11ebcdd4e448e6a90eca227e41943a
Source dataset
uspto-grants-2001_07
Patent number
US06255318B1

Reaction notes

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