2-Methylpropylenediamine → 5-[3-[(2-Amino-2-methylpropyl)amino]propyl]-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide, dihydrochloride salt

HRID 1593816Notes

Reaction equation

HRID 1593816 reaction equation
[CH3:1][C:2]([NH2:6])([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]>O1CCCC1.C(OCC)(=O)C>[ClH:7].[ClH:7].[NH2:6][C:2]([CH3:5])([CH3:1])[CH2:3][NH:4][CH2:30][CH2:29][CH2:28][C:25]1[CH:26]=[CH:27][C:8]([Cl:7])=[C:9]([CH:24]=1)[C:10]([NH:12][CH2:13][C:14]12[CH2:21][CH:20]3[CH2:19][CH:18]([CH2:17][CH:16]([CH2:22]3)[CH2:15]1)[CH2:23]2)=[O:11]

Participants

5

Reactant 2

HCID 131282-MethylpropylenediamineHCID 12988688chloro-5-[3-[(methylsulfonyl)oxy]propyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Product 1

HCID 1317248385-[3-[(2-Amino-2-methylpropyl)amino]propyl]-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide, dihydrochloride salt

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

2-Methyl-1,2-propanediamine (0.12 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 6e) in tetrahydrofuran (4 ml) and heated at 60° C. in a sealed tube for 12 h. On cooling to ambient temperature, the mixture was diluted with ethyl acetate and extracted twice with saturated sodium hydrogencarbonate solution and once with brine, dried over magnesium suflate and concentrated under reduced pressure. Purification by preperative reverse phase HPLC (eluting with a gradient of acetonitrile in 0.1% aqueous ammonium acetate/25-95%) gave the title compound as the acetate salt. Treatment with 4 M hydrochloric acid in dioxane gave the title compound as the dihydrochloride salt (0.045 g).

Workup

  1. temperatureOn cooling to ambient temperature
  2. extractionextracted twice with saturated sodium hydrogencarbonate solution and once with brine
  3. dry with materialdried over magnesium suflate
  4. concentrationconcentrated under reduced pressure
  5. customPurification by preperative reverse phase HPLC (
  6. washeluting with a gradient of acetonitrile in 0.1% aqueous ammonium acetate/25-95%)

Sources & evidence

ORD record
ord-dc1bc142732d4b3e9774529ddf45cca5
Source dataset
uspto-grants-2007_11
Patent number
US07297818B2

Reaction notes

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