Ethylamine → HCID 131726481, compound

HRID 1765529Notes

Reaction equation

HRID 1765529 reaction equation
[CH2:1]([NH2:3])[CH3:2].[Cl:4][C:5]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C@H:27]([OH:34])[CH2:28]OS(C)(=O)=O)=[CH:21][C:6]=1[C:7]([NH:9][CH2:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:8]>C(#N)C>[ClH:4].[Cl:4][C:5]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C@H:27]([OH:34])[CH2:28][NH:3][CH2:1][CH3:2])=[CH:21][C:6]=1[C:7]([NH:9][CH2:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:8]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 21107410HCID 21107410, compound

Product 1

HCID 131726481HCID 131726481, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Aqueous ethylamine (70%) (2 mL) was added to a solution of 2-chloro-5-[(3S)-3-hydroxy-4-[(methylsulfonyl)oxy]butyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide (Example 1c) (0.2 g) in acetonitrile (5 mL) and heated at 50° C. for 2.5 hours. On cooling the reaction mixture was concentrated and purified by solid phase extraction on Waters' SCX resin, eluting with ammonia in methanol (7M). Further purification by reverse phase HPLC (gradient 25–95% acetonitrile in 0.2% aqueous trifluoroacetic acid (TFA) on Symmetry™ column). The residue was dissolved in methanol (5 mL) and hydrochloric acid in 1,4-dioxane (4M, 1 mL) was added, evaporation and recrystallisation from acetonitrile, gave the titled compound (0.13 g).

Workup

  1. temperatureOn cooling the reaction mixture
  2. concentrationwas concentrated
  3. custompurified by solid phase extraction on Waters' SCX resin
  4. washeluting with ammonia in methanol (7M)
  5. customFurther purification by reverse phase HPLC (gradient 25–95% acetonitrile in 0.2% aqueous trifluoroacetic acid (TFA) on Symmetry™ column)
  6. dissolutionThe residue was dissolved in methanol (5 mL)
  7. additionhydrochloric acid in 1,4-dioxane (4M, 1 mL) was added
  8. customevaporation and recrystallisation from acetonitrile

Sources & evidence

ORD record
ord-50001f0d3b0e42db927a043d437371a7
Source dataset
uspto-grants-2007_06
Patent number
US07227038B2

Reaction notes

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