2,2,2-Trifluoroethanol → HCID 58223062, compound

HRID 2042698Notes

Reaction equation

HRID 2042698 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4](Cl)[N:3]=1.[F:10][C:11]([F:15])([F:14])[CH2:12][OH:13].N1C(C)=CC(C)=CC=1C.[NH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1.CCN(C(C)C)C(C)C.Cl.[NH2:46][CH2:47][C:48]1[CH:57]=[CH:56][C:51]([C:52]([O:54][CH3:55])=[O:53])=[CH:50][CH:49]=1>CC(C)=O.CN1C(=O)CCC1.O>[CH3:55][O:54][C:52]([C:51]1[CH:56]=[CH:57][C:48]([CH2:47][NH:46][C:2]2[N:7]=[C:6]([O:13][CH2:12][C:11]([F:15])([F:14])[F:10])[N:5]=[C:4]([NH:25][C:26]3[CH:27]=[CH:28][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:34][CH:35]=3)[N:3]=2)=[CH:49][CH:50]=1)=[O:53]

Participants

10

Reactant 6

HCID 64092,2,2-TrifluoroethanolHCID 79532,4,6-TrimethylpyridineHCID 7954Cyanuric chlorideHCID 12082Methyl 4-aminobenzoateHCID 81531DiisopropylethylamineHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochloride

Product 1

HCID 58223062HCID 58223062, compoundYield 62.6%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 2,4,6-trichloro-1,3,5-triazine (3 g) in acetone (70 mL) was added 2,2,2-trifluoroethanol (1.79 g) and 2,4,6-collidine (2.365 mL) in acetone (70.0 mL) dropwise over 1 hour. The resulting mixture was stirred at room temperature for 16 hours. All solvents were removed under vacuum to give a residue which was diluted with NMP (25 mL) and combined with methyl 4-aminobenzoate (2.71 g) and iPr2NEt (8.52 mL). After stirring at room temperature for 6 hours, methyl 4-(aminomethyl)benzoate hydrochloride (3.28 g) was added and the resulting mixture was stirred at room temperature for 16 hours. The mixture was diluted with water (300 mL) and extracted with EtOAc (2×400 mL). The organic layers were combined, washed with water (200 mL), brine (300 mL), dried over MgSO4 and concentrated. The residue was purified by recrystallization with MeOH to give methyl 4-(4-(4-(methoxycarbonyl)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (5 g).

Workup

  1. customAll solvents were removed under vacuum
  2. customto give a residue which
  3. stirringAfter stirring at room temperature for 6 hours
  4. stirringthe resulting mixture was stirred at room temperature for 16 hours
  5. extractionextracted with EtOAc (2×400 mL)
  6. washwashed with water (200 mL), brine (300 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified by recrystallization with MeOH

Sources & evidence

ORD record
ord-79b439c5a3504e7c971370c940b1e6e3
Source dataset
uspto-grants-2013_11
Patent number
US08586584B2

Reaction notes

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