(2-Amino-5-methyl-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester → HCID 18548894, compound

HRID 1266898Notes

Reaction equation

HRID 1266898 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=1[NH2:19])(C)(C)C.C(O[C:26](=[O:50])[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36]2[N:37]=[C:38]([CH2:42][O:43]C3CCCCO3)[S:39][C:40]=2[CH3:41])[CH:31]=1)=O)(C)(C)C>C1(C)C=CC=CC=1>[OH:43][CH2:42][C:38]1[S:39][C:40]([CH3:41])=[C:36]([C:32]2[CH:31]=[C:30]([C:28]3[CH2:27][C:26](=[O:50])[NH:19][C:9]4[CH:10]=[C:11]([C:15]([F:16])([F:17])[F:18])[C:12]([CH3:14])=[CH:13][C:8]=4[N:7]=3)[CH:35]=[CH:34][CH:33]=2)[N:37]=1

Participants

4

Reactant 2

HCID 67361461(2-Amino-5-methyl-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl esterHCID 69688870HCID 69688870, compound

Product 1

HCID 18548894HCID 18548894, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (2-amino-5-methyl-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester (Example J15) (0.145 g) and 3-[3-[5-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-thiazol-4-yl]-phenyl]-3-oxo-propionic acid tert.-butyl ester (Example K18) (0.18 g) in toluene (1.5 mL) was heated to 100° C. for 8 h. The mixture was cooled and evaporated in vacuum. A solution of the residue in a mixture of CH2Cl2 (2.5 mL) and trifluoroacetic acid (2.5 mL) was stirred for 0.5 h at 20° C. The mixture was evaporated in vacuum, the residual oil was dissolved in AcOEt and the solution was washed with saturated NaHCO3 solution and with brine, dried over Na2SO4 and evaporated in vacuum. The residue was triturated with CH2Cl2 to give the title compound (0.07 g) as white crystals.

Workup

  1. temperatureThe mixture was cooled
  2. customevaporated in vacuum
  3. additionA solution of the residue in a mixture of CH2Cl2 (2.5 mL) and trifluoroacetic acid (2.5 mL)
  4. customThe mixture was evaporated in vacuum
  5. dissolutionthe residual oil was dissolved in AcOEt
  6. washthe solution was washed with saturated NaHCO3 solution and with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated in vacuum
  9. customThe residue was triturated with CH2Cl2

Sources & evidence

ORD record
ord-b6b2e955bb824932b9625666926c8fb3
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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