3-Amino-1-propanol → HCID 11588111, compound

HRID 2239653Notes

Reaction equation

HRID 2239653 reaction equation
[C:1]([N:5]1[C:9](=[O:10])[C:8](Cl)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])([CH3:4])([CH3:3])[CH3:2].[OH:20][CH2:21][CH2:22][CH2:23][NH2:24]>CC#N>[C:1]([N:5]1[C:9](=[O:10])[C:8]([NH:24][CH2:23][CH2:22][CH2:21][OH:20])=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 672426272-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 11588111HCID 11588111, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-tert-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.300 g, 1.001 mmol), 3-hydroxypropyamine (0.08 ml, 1.001 mmol) and TEA (0.14 ml, 1.001 mmol) in MeCN (5 ml) was stirred at rt. After 18 h the mixture was evaporated to dryness and the residue was purified by silica gel column chromatography (Horizons Biotage) eluting with 33-80% EtOAc (+0.5% TEA) in petroleum ether 40-60° C. to give the title compound (0.145 g, 43%). 1H NMR (500 MHz, CDCl3): δ 7.55-7.50 (m, 2H), 7.46-7.42 (m, 3H), 5.77 (t, 1H), 3.62 (q, 2H), 3.01 (q, 2H), 1.74 (s, 9H), 1.63 (qt, 2H); Mass Spectrum: M−H+ 337.

Workup

  1. customAfter 18 h the mixture was evaporated to dryness
  2. customthe residue was purified by silica gel column chromatography (Horizons Biotage)
  3. washeluting with 33-80% EtOAc (+0.5% TEA) in petroleum ether 40-60° C.

Sources & evidence

ORD record
ord-4cfc5fb1ef094bdabeab7a1df08b7da0
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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