Diisopropylethylamine → 2,5-Dichloro-N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-nicotinamide

HRID 1029144Notes

Reaction equation

HRID 1029144 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:16]=[CH:15][N:14]=[C:13]3[C:8]=2[C:9]2[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=2[C:11](=[O:17])[NH:12]3)=[CH:4][CH:3]=1.[Cl:24][C:25]1[N:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:26]=1[C:27](Cl)=[O:28].CCN(C(C)C)C(C)C>O1CCOCC1.CCOC(C)=O.O>[Cl:24][C:25]1[N:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:26]=1[C:27]([NH:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:16]=[CH:15][N:14]=[C:13]3[C:8]=2[C:9]2[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=2[C:11](=[O:17])[NH:12]3)=[CH:4][CH:3]=1)=[O:28]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27999962,5-Dichloro-nicotinoyl chlorideHCID 581683671-(4-Amino-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 581683272,5-Dichloro-N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-nicotinamideYield 64.5%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 22728543Water ethylacetateSolvent

Procedure

Compound 137 (40 mg, 0.13 mmol), 2,5-dichloro-nicotinoyl chloride (28 mg, 0.13 mmol), and DIEA (0.02 mL, 0.13 mmol) were suspended in dioxane (2 mL), and stirred overnight at room temperature. The reaction mixture was diluted with EtOAc/H2O. The resulting precipitate was filtered, washed with EtOAc/H2O, and dried under vacuum to provide 180 (40 mg, 64% yield) as a white solid. LC-MS (M+H=478, obsd.=478).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with EtOAc/H2O
  3. customdried under vacuum

Sources & evidence

ORD record
ord-6086b94094634432a2e6dc0c1eea5f42
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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