HCID 59242107, compound → HCID 59242053, compound

HRID 1876147Notes

Reaction equation

HRID 1876147 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]([CH3:24])[C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]([CH3:23])[N:14]=2)=[CH:8][CH:7]=1>C1COCC1.P([O-])([O-])([O-])=O>[CH3:24][N:12]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([CH3:23])[N:14]=1)[C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:25])=[O:2])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 59242107HCID 59242107, compound

Product 1

HCID 59242053HCID 59242053, compound

Reagents, catalysts & solvents 2

HCID 1061PhosphateSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {4-[methyl-(2-methyl-quinazolin-4-yl)-amino]-phenoxy}-acetic acid methyl ester (200 mg, 0.59 mmol) in THF (5 mL) was added potassium trimethylsilanoate (770 mg, 6 mmol). The mixture was stirred at ambient temperature for 1 h. The mixture was diluted with phosphate buffer (pH=5.5) and extracted with EtOAc (3×). The pH of the aqueous phase was raised to 6 with NaOH and was extracted with EtOAc (3×). The combined organics were dried over MgSO4, filtered and concentrated. The title compound was used without further purification. 1H NMR (DMSO-d6) δ 7.64 (d, 1H), 7.59 (t, 1H), 7.20 (d, 2H), 7.03 (t, 1H), 7.0-6.9 (m, 3H), 4.85 (s, 2H), 3.50 (s, 3H), 2.60 (s, 3H); LC-MS (ESI+; 324 ([M+H]+)).

Workup

  1. extractionextracted with EtOAc (3×)
  2. temperatureThe pH of the aqueous phase was raised to 6 with NaOH
  3. extractionwas extracted with EtOAc (3×)
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe title compound was used without further purification

Sources & evidence

ORD record
ord-e1fd307176544e26b168c82ae03c426e
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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