3-Methoxyaniline → HCID 57976006, compound

HRID 1865204Notes

Reaction equation

HRID 1865204 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:22](=[CH:23][CH:24]=1)[NH:21][C:20]([C:25](O)=[O:26])=[CH:19]2.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([NH2:36])[CH:33]=[CH:34][CH:35]=1.CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH3:28][O:29][C:30]1[CH:31]=[C:32]([NH:36][C:25]([C:20]2[NH:21][C:22]3[C:18]([CH:19]=2)=[CH:17][C:16]([O:15][C:6]2[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=2)=[CH:24][CH:23]=3)=[O:26])[CH:33]=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 108243-MethoxyanilineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 69018669HCID 69018669, compound

Product 1

HCID 57976006HCID 57976006, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(6,7-dimethoxy-quinolin-4-yloxy)-1H-indole-2-carboxylic acid (0.1 g, 0.27 mmol, from step b), 3-methoxy-phenylamine (68 mg, 0.55 mmol) and DIEA (0.1 mL, 0.55 mmol) in 3 mL of DMF was added PyBOP (0.29, 0.55 mmol, Aldrich) at RT. The reaction was stirred at RT for 16 h. The mixture was diluted with 50 mL of EtOAc, and the resulted solution was washed with 30 mL of satd. NaHCO3 followed by 30 mL of brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by silica gel column chromatography (50% to 100% EtOAc/hexane) to afford off-white solid as desired product. MS (ESI pos. ion) m/z: 470 (M+H). Calc'd Exact Mass for C27H23N3O5: 469.49.

Workup

  1. washthe resulted solution was washed with 30 mL of satd
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified by silica gel column chromatography (50% to 100% EtOAc/hexane)

Sources & evidence

ORD record
ord-276ea27fd5d14ca1a7750539d4d49413
Source dataset
uspto-grants-2009_12
Patent number
US07626030B2

Reaction notes

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