Pyridine → N-(2-(tert-Butyl)-5-hydroxy-4-(1-hydroxy-2-methylpropan-2-yl)phenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

HRID 2401657Notes

Reaction equation

HRID 2401657 reaction equation
C(=O)([O-])OC[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][C:5]=1[C:15]([CH3:23])([CH3:22])[CH2:16][O:17]C(OC)=O.[O:26]=[C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=[C:28]1[C:37](O)=[O:38].N1C=CC=CC=1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)[O:50]1)CC.C[O-].[Na+]>CC1OCCC1.O>[C:11]([C:7]1[CH:6]=[C:5]([C:15]([CH3:22])([CH3:23])[CH2:16][OH:17])[C:4]([OH:50])=[CH:9][C:8]=1[NH:10][C:37]([C:28]1[C:27](=[O:26])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)=[O:38])([CH3:12])([CH3:13])[CH3:14]

Participants

8

Reactant 5

HCID 1049PyridineHCID 111923Propylphosphonic anhydrideHCID 2208754-Quinolone-3-carboxylic acidHCID 10942334Sodium MethoxideHCID 86663357[5-Amino-4-tert-butyl-2-(2-methoxycarbonyloxy-1,1-dimethyl-ethyl)phenyl]methyl carbonate

Product 1

HCID 46897962N-(2-(tert-Butyl)-5-hydroxy-4-(1-hydroxy-2-methylpropan-2-yl)phenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 73012-MethyltetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a mixture of [5-amino-4-tert-butyl-2-(2-methoxycarbonyloxy-1,1-dimethyl-ethyl)phenyl]methyl carbonate (103 mg, 0.29 mmol), 4-oxo-1,4-dihydroquinoline-3-carboxylic acid (50 mg, 0.26 mmol), and pyridine (42 mg, 0.53 mmol) in 2-MeTHF (3.0 mL) was charged T3P as a 50 wt % solution in 2-MeTHF (286 mg, 0.45 mmol). The mixture was heated to 50° C. for 18 h. After cooling to ambient temperature, the mixture was diluted with water. The organic phase was separated and again washed with water. Sodium methoxide (39 mg, 0.72 mmol) was charged to the organic phase and the solution stirred for 2 hours. The reaction was quenched with 1N HCl, and after separating the phases, the organic phase was washed with 0.1N HCl. The organic phase was than dried in vacuo to yield Compound 27 as a solid. The 1H-NMR spectrum was consistent with that reported above.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customThe organic phase was separated
  3. washagain washed with water
  4. customThe reaction was quenched with 1N HCl
  5. customafter separating the phases
  6. washthe organic phase was washed with 0.1N HCl
  7. customthan dried in vacuo

Sources & evidence

ORD record
ord-85578e273e1a44c38ebbcfe8ebbfb69e
Source dataset
uspto-grants-2014_08
Patent number
US08796308B2

Reaction notes

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