Trifluoroacetic acid → 5-Amino-1-(1-(7-methoxyquinolin-4-yloxy)-2-methylpropan-2-yl)pyridin-2(1H)-one

HRID 1878723Notes

Reaction equation

HRID 1878723 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][CH2:14][C:15]([N:18]3[C:23](=[O:24])[CH:22]=[CH:21][C:20]([NH:25]C(=O)OC(C)(C)C)=[CH:19]3)([CH3:17])[CH3:16])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:25][C:20]1[CH:21]=[CH:22][C:23](=[O:24])[N:18]([C:15]([CH3:16])([CH3:17])[CH2:14][O:13][C:7]2[C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:10]=[CH:9][CH:8]=2)[CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59843045tert-Butyl 1-(1-(7-methoxyquinolin-4-yloxy)-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridin-3-ylcarbamate

Product 1

HCID 688167765-Amino-1-(1-(7-methoxyquinolin-4-yloxy)-2-methylpropan-2-yl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 1-(1-(7-methoxyquinolin-4-yloxy)-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridin-3-ylcarbamate (55 mg, 125 μmol) in CH2Cl2 (1 mL) was added TFA (3 mL). After 90 min at 23° C., the solvents were removed under reduced pressure. The residue was partitioned between CH2Cl2 and NaOH (1 M). The organic was dried over MgSO4, reduced to a brown solid under reduced pressure. MS (ESI pos. ion) m/z (MH+): 340. Calc'd exact mass for C19H21N3O3: 339. 1H NMR (400 MHz, Chloroform-d) 8 ppm 1.65 (s, 6 H) 2.35 (s, 2 H) 3.94 (s, 3 H) 3.99 (s, 2 H) 6.30 (d, J=5.52 Hz, 1 H) 6.64 (d, J=9.03 Hz, 1 H) 7.09-7.20 (m, 4 H) 7.29-7.36 (m, 2 H) 7.64 (s, 1 H) 7.82 (d, J=9.03 Hz, 1 H) 8.31-8.39 (m, 1 H).

Workup

  1. customthe solvents were removed under reduced pressure
  2. customThe residue was partitioned between CH2Cl2 and NaOH (1 M)
  3. dry with materialThe organic was dried over MgSO4

Sources & evidence

ORD record
ord-bf472ddfb6c34fe4805e161b2b9411bd
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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