Ethyl isocyanate → HCID 11156826, compound

HRID 1925266Notes

Reaction equation

HRID 1925266 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[N:9]=[CH:8][CH:7]=[C:6]2[O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]=[C:29]([NH2:34])[CH:28]=[CH:27]2.CCN(CC)CC.[CH2:42]([N:44]=[C:45]=[O:46])[CH3:43]>CN(C=O)C>[CH2:42]([NH:44][C:45]([NH:34][C:29]1[CH:28]=[CH:27][C:26]2[C:31](=[CH:32][CH:33]=[C:24]([O:23][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][N:17]5[CH2:22][CH2:21][O:20][CH2:19][CH2:18]5)=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)[CH:25]=2)[CH:30]=1)=[O:46])[CH3:43]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 67519891HCID 67519891, compound

Product 1

HCID 11156826HCID 11156826, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-[6-methoxy-7-(3-morpholin-4-ylpropoxy)-4-quinolyloxy]-2-naphthylamine (prepared similar to that described in Example 1, Step c) (46.0 mg, 0.1 mmol) in anhydrous DMF (5 mL, Aldrich) was added Et3N (50.5 mg, 0.5 mmol, Aldrich) and ethyl isocyanate (35.5 mg, 0.5 mmol, Aldrich) at RT. The reaction was stirred at RT for 16 h, then was quenched with saturated aqueous solution of NaHCO3 (20 mL) and extracted with EtOAc (2×30 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (FPNH-25S, Biotage, EtOAc) to give the title compound as white solid. MS (ESI, pos. ion) m/z: 531.3 (M+1); 529.3 (M−1). Calc'd for C30H33N4O5−530.25.

Workup

  1. customwas quenched with saturated aqueous solution of NaHCO3 (20 mL)
  2. extractionextracted with EtOAc (2×30 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (FPNH-25S, Biotage, EtOAc)

Sources & evidence

ORD record
ord-bb572497788146aaa4461e5fc35d0668
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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