Triethylamine → [1,6]Naphthyridine-2-carboxylic acid (trans-2-phenyl-cyclopropyl)-amide

HRID 1383413Notes

Reaction equation

HRID 1383413 reaction equation
Cl.[C:2]1([C@@H:8]2[CH2:10][C@H:9]2[NH2:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[N:19]1[C:28]2[C:23](=[CH:24][N:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[C:29](O)=[O:30].O.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[C:2]1([C@@H:8]2[CH2:10][C@H:9]2[NH:11][C:29]([C:20]2[CH:21]=[CH:22][C:23]3[C:28](=[CH:27][CH:26]=[N:25][CH:24]=3)[N:19]=2)=[O:30])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 7359081,6-Naphthyridine-2-carboxylic acidHCID 2723716Tranylcypromine hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 57280006[1,6]Naphthyridine-2-carboxylic acid (trans-2-phenyl-cyclopropyl)-amideYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring mixture of trans-2-phenylcyclopropylamine hydrochloride (75.3 mg, 0.431) in anhydrous DMF (1.0 mL) was added triethylamine (60.0 μL, 0.431 mmol). After 5 minutes, 2-[1,6]naphthyridinecarboxylic acid (50 mg, 0.287 mmol), 1-hydroxybenzotriazole hydrate (42.7 mg, 0.316 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarboiimide hydrochloride (61.8 mg, 0.316 mmol) were added sequentially. 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 100% ethyl acetate) afforded the desired product as a white solid (79.2 mg, 95%): m.p. 123-124° C.

Workup

  1. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-82962b95f3dc45b880e302ec360108de
Source dataset
uspto-grants-2001_07
Patent number
US06255318B1

Reaction notes

Loading…