2-Pyridinemethanamine → HCID 22980443, compound

HRID 1586516Notes

Reaction equation

HRID 1586516 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)-3ethylcarboiimide 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-d86d8eb9e85b406f8b4191a1c502a747
Source dataset
uspto-grants-1999_08
Patent number
US05945431

Reaction notes

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