Isopropylamine → HCID 131726482, compound

HRID 1765530Notes

Reaction equation

HRID 1765530 reaction equation
[CH3:1][CH:2]([NH2:4])[CH3:3].[Cl:5][C:6]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C@H:28]([OH:35])[CH2:29]OS(C)(=O)=O)=[CH:22][C:7]=1[C:8]([NH:10][CH2:11][C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2)=[O:9]>C(#N)C>[ClH:5].[Cl:5][C:6]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C@H:28]([OH:35])[CH2:29][NH:4][CH:2]([CH3:3])[CH3:1])=[CH:22][C:7]=1[C:8]([NH:10][CH2:11][C:12]12[CH2:21][CH:16]3[CH2:15][CH:14]([CH2:20][CH:18]([CH2:17]3)[CH2:19]1)[CH2:13]2)=[O:9]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 21107410HCID 21107410, compound

Product 1

HCID 131726482HCID 131726482, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

1-Methylethylamine (3 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) (0.22 g) in acetonitrile (10 mL) and heated at 50° C. for 18 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 on Symmetry™ column). The residue was dissolved in methanol (5 mL) and hydrochloric acid in dioxane (4M, 1 mL) was added, evaporation and recrystallisation from MeCN, gave the titled compound as the hydrochloric acid salt (30 mg).

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 on Symmetry™ column)
  6. dissolutionThe residue was dissolved in methanol (5 mL)
  7. additionhydrochloric acid in dioxane (4M, 1 mL) was added
  8. customevaporation and recrystallisation from MeCN

Sources & evidence

ORD record
ord-f21d28511d0a4707a1707d9adf4b537b
Source dataset
uspto-grants-2007_06
Patent number
US07227038B2

Reaction notes

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