Trifluoroacetic acid → N-[2-(4-Carbomethoxymethoxyphenyl)-1-methylethyl]-2-(2-trifluoromethyl-5-methyl-thiazol-4-yl)morpholine

HRID 1451456Notes

Reaction equation

HRID 1451456 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[S:4][C:5]([CH3:12])=[C:6]([C:8](=[O:11])[CH2:9]Br)[N:7]=1.O[CH2:16][CH2:17][NH:18][CH:19]([CH3:33])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:23][CH:22]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[C:29]([CH2:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][CH:19]([N:18]2[CH2:17][CH2:16][O:11][CH:8]([C:6]3[N:7]=[C:3]([C:2]([F:14])([F:13])[F:1])[S:4][C:5]=3[CH3:12])[CH2:9]2)[CH3:33])=[CH:22][CH:23]=1)([O:31][CH3:32])=[O:30]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14347764HCID 14347764, compoundHCID 199742062-Trifluoromethyl-5-methyl-4-bromoacetyl-thiazole

Product 1

HCID 19974341N-[2-(4-Carbomethoxymethoxyphenyl)-1-methylethyl]-2-(2-trifluoromethyl-5-methyl-thiazol-4-yl)morpholine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared by analogy to Example 32 by reaction of 4.2 g (0.0146 mol) of 2-trifluoromethyl-5-methyl-4-bromoacetyl-thiazole with 8 g (0.03 mol) of N-(2-hydroxyethyl)-2-(4-carbomethoxymethoxyphenyl)-1-methylethylamine in methylene chloride by stirring at room temperature for 20 hours and heating under reflux for 2 hours. The reduction is carried out in 28 ml of trifluoroacetic acid using 2.4 g (0.02 mol) of triethylsilane. The crude product is purified on a silica gel column using toluene/ethyl acetate=7:3 as eluant.

Workup

  1. temperatureheating
  2. temperatureunder reflux for 2 hours
  3. customThe crude product is purified on a silica gel column

Sources & evidence

ORD record
ord-33b2123682dc43808410403c946438b8
Source dataset
uspto-grants-1997_02
Patent number
US05604225

Reaction notes

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