4-(2-Aminoethoxy)benzamide → 1-[beta-(4-Aminocarbonylphenoxy)-ethylamino]-3-(5-4'-methylhexylaminocarbonylthiazol-2-oxy)-2-propanol

HRID 372190Notes

Reaction equation

HRID 372190 reaction equation
[NH2:1][C:2]([C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10][NH2:11])=[CH:6][CH:5]=1)=[O:3].[O:14]1[CH:16]([CH2:17][O:18][C:19]2[S:20][C:21]([C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH:30]([CH3:33])[CH2:31][CH3:32])=[O:25])=[CH:22][N:23]=2)[CH2:15]1>C(O)C>[NH2:1][C:2]([C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10][NH:11][CH2:15][CH:16]([OH:14])[CH2:17][O:18][C:19]2[S:20][C:21]([C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH:30]([CH3:33])[CH2:31][CH3:32])=[O:25])=[CH:22][N:23]=2)=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 126663984-(2-Aminoethoxy)benzamideHCID 20328376N-(4-Methylhexyl)-2-[(oxiran-2-yl)methoxy]-1,3-thiazole-5-carboxamide2×

Product 1

HCID 203284641-[beta-(4-Aminocarbonylphenoxy)-ethylamino]-3-(5-4'-methylhexylaminocarbonylthiazol-2-oxy)-2-propanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

This example illustrates further methods according to the invention of preparing further compounds of formula I of the invention. In this example 1 g. of β-(4-aminocarbonylphenoxy)-ethylamine (Cox et al, J. Med. Chem., v. 16, No. 11 (1973)) is added to a solution containing 0.4 g. of 1,2-epoxy-3-(5-4'-methylhexylaminocarbonylthiazol-2-oxy)-propane in 20 ml. of anhydrous absolute ethanol at 20° C. The resulting mixture is monitored by thin-layer chromatographic analysis and allowed to stand until conversion of the 1,2-epoxy-3-(5-4'-methylhexylaminocarbonylthiazol-2-oxy)-propane is essentially complete. The mixture is then evaporated to dryness yielding a crude residue which is then further purified by thin-layer chromatography on silica gel yielding 1-[β-(4-aminocarbonylphenoxy)-ethylamino]-3-(5-4'-methylhexylaminocarbonylthiazol-2-oxy)-2-propanol.

Workup

  1. customaccording to the invention of preparing further compounds of formula I of the invention
  2. addition11 (1973)) is added to a solution
  3. additioncontaining 0.4 g
  4. customat 20° C
  5. customThe mixture is then evaporated to dryness
  6. customyielding a crude residue which
  7. customis then further purified by thin-layer chromatography on silica gel

Sources & evidence

ORD record
ord-0107cc5016b44a66a15f2578b2d24540
Source dataset
uspto-grants-1978_05
Patent number
US04089865

Reaction notes

Loading…