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

HRID 2210388Notes

Reaction equation

HRID 2210388 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[O:13])[CH2:11]Br)[N:9]=1)(=[O:3])[CH3:2].O[CH2:15][CH2:16][NH:17][CH:18]([CH3:32])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:22][CH:21]=1.C(N(CC)CC)C.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl.CO>[C:28]([CH2:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH:18]([N:17]2[CH2:16][CH2:15][O:13][CH:10]([C:8]3[N:9]=[C:5]([NH:4][C:1]([CH3:2])=[O:3])[S:6][CH:7]=3)[CH2:11]2)[CH3:32])=[CH:21][CH:22]=1)([O:30][CH3:31])=[O:29]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 12052TriethylsilaneHCID 14347764HCID 14347764, compoundHCID 19974225N-[4-(Bromoacetyl)-1,3-thiazol-2-yl]acetamide

Product 1

HCID 19974192N-[2-(4-carbomethoxymethoxyphenyl)1-methylethyl]-2-(2-acetamino-thiazol-4-yl)morpholine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Prepared by analogy to Example 32 by reaction of 2.23 g (0.0085 mol) of 2-acetylamino-4-bromoacetylthiazole with 2.26 g of (0.0085 mol) of N-(2-hydroxy-ethyl)-2-(4-carbomethoxymethoxyphenyl)-1-methylethylamine and 0.86 g (0.0085 mol) of triethylamine in 30 ml of methylene chloride and 30 ml of methanol for 20 hours at room temperature. The reduction is carried out in 9 ml of trifluoroacetic acid using 1.48 g (0.0128 mol) of triethylsilane. The crude product is purified on a silica gel column using ethyl acetate/methanol =9:1 as eluant.

Workup

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

Sources & evidence

ORD record
ord-fc0c67e0aacc4272be54afdd4c9a323f
Source dataset
uspto-grants-1995_10
Patent number
US05457205

Reaction notes

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