1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-Benzyl-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid (2-oxazol-2-yl-4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridin-3-ylmethyl)-amide

HRID 1887839Notes

Reaction equation

HRID 1887839 reaction equation
[CH2:1]([N:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=O)=[CH:10][C:9]1=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)CCCN=C=NCC.N1(O)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH2:48][CH2:49][C:50]1[C:59](=[O:60])[C:58]2[C:53](=[N:54][CH:55]=[CH:56][CH:57]=2)[N:52]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[C:51]=1[C:67]1[O:68][CH:69]=[CH:70][N:71]=1>C(Cl)Cl>[O:68]1[CH:69]=[CH:70][N:71]=[C:67]1[C:51]1[N:52]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[C:53]2[C:58]([C:59](=[O:60])[C:50]=1[CH2:49][NH:48][C:14]([C:11]1[CH:12]=[CH:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:9](=[O:17])[CH:10]=1)=[O:16])=[CH:57][CH:56]=[CH:55][N:54]=2

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 181796161-Benzyl-2-oxo-1,2-dihydropyridine-4-carboxylic acidHCID 712085053-(aminomethyl)-2-(oxazol-2-yl)-1-phenyl-1,8-naphthyridin-4(1H)-one2×

Product 1

HCID 712173321-Benzyl-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid (2-oxazol-2-yl-4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridin-3-ylmethyl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 mL round-bottomed flask, 1-benzyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid (21 mg, 0.93 mmol), 1-(3-dimethylaminopropyl-3-ethylcarbodiimide (23.0 mg, 0.148 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (20.0 mg, 0.148 mmol) and N,N-diisopropylethylamine were combined with methylene chloride (5 mL). The reaction mixture was stirred at room temperature for 10 min. After this time, 3-(aminomethyl)-2-(oxazol-2-yl)-1-phenyl-1,8-naphthyridin-4(1H)-one (intermediate B) was added. The reaction mixture was stirred at room temperature over the weekend. The reaction mixture was partitioned between methylene chloride and water. The organic phase was dried over sodium sulfate, then filtered and concentrated. The crude product was purified using flash chromatography (Isco, 0% ethyl acetate-hexanes ramped to 70% ethyl acetate-hexanes) to afford 1-Benzyl-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid (2-oxazol-2-yl-4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridin-3-ylmethyl)-amide as a light brown powder (12 mg). MS calcd. for C31H24N5O4 [(M+H)+] 530.2, obsd. 530.3

Workup

  1. stirringThe reaction mixture was stirred at room temperature over the weekend
  2. customThe reaction mixture was partitioned between methylene chloride and water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-1e65ab25ab8d4aceb653d697328cc32f
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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