(1R,2S)-2-Fluorocyclopropan-1-amine → 6-((6,7-bis(methoxy)-4-quinolinyl)oxy)-N-((1R,2S)-2-fluorocyclopropyl)-1-naphthalenecarboxamide

HRID 1925280Notes

Reaction equation

HRID 1925280 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([C:26](Cl)=[O:27])=[CH:21][CH:20]=[CH:19]2.[F:29][C@H:30]1[CH2:32][C@H:31]1[NH2:33]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([C:26]([NH:33][C@@H:31]1[CH2:32][C@@H:30]1[F:29])=[O:27])=[CH:21][CH:20]=[CH:19]2

Participants

4

Reactant 2

HCID 10313105(1R,2S)-2-Fluorocyclopropan-1-amineHCID 248229436-(6,7-Dimethoxyquinolin-4-yloxy)-1-naphthoyl chloride

Product 1

HCID 598132786-((6,7-bis(methoxy)-4-quinolinyl)oxy)-N-((1R,2S)-2-fluorocyclopropyl)-1-naphthalenecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(6,7-Dimethoxyquinolin-4-yloxy)-1-naphthoyl chloride (200 mg, 0.50 mmol) was suspended in CH2Cl2 and TEA (210 μL, 1.5 mmol) was added. The mixture was blanketed with nitrogen, cis-2-fluorocyclopropylamine (131 mg, 0.54 mmol) was added and the reaction was stirred at RT for 1 h. The mixture was washed with water, dried with Na2SO4, filtered and concentrated in-vacuo. The residue was purified by column chromatography to give the title compounds. MS (ESI pos. ion) m/z: 433.2 (M+H). Calc'd for C28H21FN2O4−432.46.

Workup

  1. additionwas added
  2. washThe mixture was washed with water
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in-vacuo
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-29ff089c74694d84934ce700aba8d248
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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