4-Amino-3-ethoxy-5-ethoxycarbonylisothiazole-1,1-dioxide → ethyl 4-amino-3-[[2-hydroxy-3-[[3-(piperidin-1-ylmethyl)phenyl]methoxy]propyl]amino]-1,1-dioxo-1,2-thiazole-5-carboxylate

HRID 542788Notes

Reaction equation

HRID 542788 reaction equation
[OH:1][CH:2]([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:9]=1)[CH2:3][NH2:4].[NH2:21][C:22]1[C:23](OCC)=[N:24][S:25](=[O:33])(=[O:32])[C:26]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(#N)C>[OH:1][CH:2]([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:9]=1)[CH2:3][NH:4][C:23]1[C:22]([NH2:21])=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[S:25](=[O:32])(=[O:33])[N:24]=1

Participants

4

Reactant 2

HCID 128421834-Amino-3-ethoxy-5-ethoxycarbonylisothiazole-1,1-dioxideHCID 135354772-Hydroxy-3-[3-(1-piperidylmethyl)benzyloxy]propylamine

Product 1

HCID 178469831ethyl 4-amino-3-[[2-hydroxy-3-[[3-(piperidin-1-ylmethyl)phenyl]methoxy]propyl]amino]-1,1-dioxo-1,2-thiazole-5-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.39 g (5 mmol) of 2-hydroxy-3-[3-(1-piperidylmethyl)benzyloxy]propylamine are added dropwise to a suspension of 1.24 g (5 mmol) of 4-amino-3-ethoxy-5-ethoxycarbonylisothiazole-1,1-dioxide in 10 ml of acetonitrile and the mixture is stirred for 5 hours at room temperature. The residue obtained after evaporation of the solvent under vacuum is chromatographed with methanol against silica gel. The main fraction yields 2.06 g (86%) of the title compound.

Workup

  1. customThe residue obtained
  2. customafter evaporation of the solvent under vacuum
  3. customis chromatographed with methanol against silica gel

Sources & evidence

ORD record
ord-6a69faa89e73425a805b3652d7c47417
Source dataset
uspto-grants-1987_04
Patent number
US04659721

Reaction notes

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