2-Thiophenecarboxylic acid → HCID 11178973, compound

HRID 1925247Notes

Reaction equation

HRID 1925247 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][CH:9]=[C:8]2[O:17][C:18]1[C:19]([F:29])=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([NH2:28])[CH:22]=[CH:21]2.[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[C:35](O)=[O:36].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>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][CH:9]=[C:8]2[O:17][C:18]1[C:19]([F:29])=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([NH:28][C:35]([C:31]1[S:30][CH:34]=[CH:33][CH:32]=1)=[O:36])[CH:22]=[CH:21]2

Participants

7

Reactant 4

HCID 107002-Thiophenecarboxylic acidHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 67520359HCID 67520359, compound

Product 1

HCID 11178973HCID 11178973, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(6,7-dimethoxy-4-quinolyloxy)-5-fluoro-2-naphthylamine 2HCl (Step c, 200 mg, 0.46 mmol), thiophene-2-carboxylic acid (120 mg, 0.91 mmol, Aldrich) and DIEA (353 mg, 2.74 mmol, Aldrich) in dry DMF was added PyBOP (476 mg, 0.91 mmol, Fluka) at RT. The reaction was stirred for 16 h. It was diluted with 40 mL of EtOAc and washed with saturated aqueous NaHCO3, followed by brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc) to give the title compound as a yellow solid. MS (ESI, pos. ion) m/z: 475.0 (M+1). Mass Calc'd for C26H19FN2O4S: 474.10.

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (EtOAc)

Sources & evidence

ORD record
ord-ace42dda5f1340a7af960afddbe25aa6
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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