2-Propanol, 1-amino-2-methyl- → 2-Chloro-5-[3-[(2-hydroxy-2-methylpropyl)amino]propyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide, acetate salt

HRID 1816049Notes

Reaction equation

HRID 1816049 reaction equation
[OH:1][C:2]([CH3:6])([CH3:5])[CH2:3][NH2:4].[Cl:7][C:8]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30]OS(C)(=O)=O)=[CH:24][C:9]=1[C:10]([NH:12][CH2:13][C:14]12[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2)=[O:11]>C(O)CCC.C(OCC)(=O)C>[C:2]([OH:1])(=[O:11])[CH3:6].[Cl:7][C:8]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][NH:4][CH2:3][C:2]([OH:1])([CH3:6])[CH3:5])=[CH:24][C:9]=1[C:10]([NH:12][CH2:13][C:14]12[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2)=[O:11]

Participants

5

Reactant 2

HCID 951022-Propanol, 1-amino-2-methyl-HCID 12988688chloro-5-[3-[(methylsulfonyl)oxy]propyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Product 1

HCID 101850252-Chloro-5-[3-[(2-hydroxy-2-methylpropyl)amino]propyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide, acetate salt

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

2-Hydroxy-2-methyl-1-propylamine [prepared according to Journal American Chemical Society (1941), 63, p1034] (0.25 ml) was added to a solution of 2-chloro-5-[3-[(methylsulfonyl)oxy]propyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.250 g, Example 6 e) in butan-1-ol (8 ml) and heated at 100° C. in a sealed tube for 24 h. On cooling to ambient temperature, the mixture was diluted with ethyl acetate and extracted twice with saturated aqueous sodium hydrogencarbonate solution and once with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by solid phase extraction on SCX resin and preparative reverse phase HPLC (eluting with a gradient of acetonitrile in 0.1% aqueous ammonium acetate/25-95%) to give the title compound as the acetate salt (0.160 g).

Workup

  1. temperatureOn cooling to ambient temperature
  2. extractionextracted twice with saturated aqueous sodium hydrogencarbonate solution and once with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by solid phase extraction on SCX resin and preparative reverse phase HPLC (
  6. washeluting with a gradient of acetonitrile in 0.1% aqueous ammonium acetate/25-95%)

Sources & evidence

ORD record
ord-c9e495b613b641bc83e7e2814183ca47
Source dataset
uspto-grants-2005_04
Patent number
US06881754B2

Reaction notes

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