Cyclobutylamine → N-cyclobutyl-1,6-naphthyridine-2-carboxamide

HRID 1713130Notes

Reaction equation

HRID 1713130 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.[CH:14]1([NH2:18])[CH2:17][CH2:16][CH2:15]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[CH:14]1([NH:18][C:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[N:7][CH:6]=3)[N:1]=2)=[O:13])[CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 75645CyclobutylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7359081,6-Naphthyridine-2-carboxylic acid

Product 1

HCID 57420578N-cyclobutyl-1,6-naphthyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,6-naphthyridine-2-carboxylic acid (188 mg, 1.08 mmol), cyclobutylamine (114 mg, 1.6 mmol), BOP (708 mg, 1.6 mmol) and TEA (0.45 ml, 3.2 mmol) in DCM (15 ml) is stirred at rt overnight. The solvent is removed in vacuo and the residue is partitioned between water (20 mL) and EtOAc (20 mL). The layers are separated and the aqueous layer is extracted with EtOAc (10 ml). The combined extracts are washed with brine (10 mL), dried and evaporated. The residue is purified by PTLC to give the title compound as a light yellow oil; MS (M+1): 228.2.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between water (20 mL) and EtOAc (20 mL)
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (10 ml)
  5. washThe combined extracts are washed with brine (10 mL)
  6. customdried
  7. customevaporated
  8. customThe residue is purified by PTLC

Sources & evidence

ORD record
ord-c3ae22cb6a404333a31fc828bf02d7e3
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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