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 719634Notes

Reaction equation

HRID 719634 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 sulfate and concentrated under reduced pressure. Purification by preparative 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 4M 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 sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification by preparative reverse phase HPLC (
  6. washeluting with a gradient of acetonitrile in 0.1% aqueous ammonium acetate/25–95%)

Sources & evidence

ORD record
ord-d1e12b11ac884db794e379a2cb74e585
Source dataset
uspto-grants-2006_11
Patent number
US07132457B2

Reaction notes

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