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

HRID 2210389Notes

Reaction equation

HRID 2210389 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[O:10])[CH2:8]Br)[N:6]=1.O[CH2:12][CH2:13][NH:14][CH:15]([CH3:29])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=1.C(=O)([O-])O.[K+].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>CC(C)=O>[C:25]([CH2:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][CH:15]([N:14]2[CH2:13][CH2:12][O:10][CH:7]([C:5]3[N:6]=[C:2]([Cl:1])[S:3][CH:4]=3)[CH2:8]2)[CH3:29])=[CH:18][CH:19]=1)([O:27][CH3:28])=[O:26]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516893Potassium BicarbonateHCID 143477622-Chloro-4-bromoacetyl-thiazoleHCID 14347764HCID 14347764, compound

Product 1

HCID 19974190N-[2-(4-Carbomethoxymethoxyphenyl)-1-methylethyl]-2-(2-chloro-thiazol-4-yl)morpholine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Prepared by analogy to Example 32 by reaction of 5 g (0.0208 mol) of 2-chloro-4-bromoacetyl-thiazole with 5.6 g (0.021 mol) of N-(2-hydroxyethyl)-2-(4-carbomethoxymethoxyphenyl)-1-methylethylamine in 200 ml of acetone and 6.3 g (0.063 mol) of potassium hydrogen carbonate over 20 hours at room temperature. The reduction is carried out in 41 ml of trifluoroacetic acid using 3.5 g (0.029 mol) of triethylsilane for 24 hours. The crude product is purified on a silica gel column using methylene chloride/methanol =20:1 as eluant.

Workup

  1. customThe crude product is purified on a silica gel column

Sources & evidence

ORD record
ord-09a01a524fae4451945fec36a25ac751
Source dataset
uspto-grants-1995_10
Patent number
US05457205

Reaction notes

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