N-Methyl-1-(2-methyl-2,3-dihydro-1H-isoindol-5-yl)methanamine → HCID 46176238, compound

HRID 469107Notes

Reaction equation

HRID 469107 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH2:15][C:16]2[O:20][C:19]([C:21]([O:23]CC)=O)=[N:18][N:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:26])[CH:4]=1.[CH3:27][NH:28][CH2:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[CH2:35][N:34]([CH3:39])[CH2:33]2>ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:26])[C:6]([S:10]([N:13]([CH2:15][C:16]2[O:20][C:19]([C:21]([N:28]([CH3:27])[CH2:29][C:30]3[CH:31]=[C:32]4[C:36](=[CH:37][CH:38]=3)[CH2:35][N:34]([CH3:39])[CH2:33]4)=[O:23])=[N:18][N:17]=2)[CH3:14])(=[O:11])=[O:12])=[C:7]([CH3:9])[CH:8]=1

Participants

4

Reactant 2

HCID 28063469N-Methyl-1-(2-methyl-2,3-dihydro-1H-isoindol-5-yl)methanamineHCID 58393140HCID 58393140, compound

Product 1

HCID 46176238HCID 46176238, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3,4-oxadiazole-2-carboxylate (30 mg, 0.081 mmol) and N-methyl-1-(2-methyl-2,3-dihydro-1H-isoindol-5-yl)methanamine (29 mg, 0.162 mmol) were dissolved in DCE (5 mL) and stirred at 0° C. prior to being degassed with N2. Trimethylaluminium (2M in toluene, 80 μl) was added dropwise to this solution. Upon completion of addition, the reaction was heated to 60° C. and stirred for 1 h. The reaction was cooled, and saturated aqueous NaHCO3 (10 mL) was added. The aqueous layer was extracted with DCM (3×10 mL) and the combined organic extracts dried over Na2SO4 and concentrated in vacuo. The resulting brown oil was purified by FCC, eluting with 99:1 DCM:7M NH3 in MeOH followed by purification using prep method D to afford the title compound.

Workup

  1. customto being degassed with N2
  2. additionTrimethylaluminium (2M in toluene, 80 μl) was added dropwise to this solution
  3. additionUpon completion of addition
  4. temperaturethe reaction was heated to 60° C.
  5. stirringstirred for 1 h
  6. temperatureThe reaction was cooled
  7. additionsaturated aqueous NaHCO3 (10 mL) was added
  8. extractionThe aqueous layer was extracted with DCM (3×10 mL)
  9. dry with materialthe combined organic extracts dried over Na2SO4
  10. concentrationconcentrated in vacuo
  11. customThe resulting brown oil was purified by FCC
  12. washeluting with 99:1 DCM
  13. custom7M NH3 in MeOH followed by purification

Sources & evidence

ORD record
ord-bcfacc5c32f848549fe25c4ed6d0017f
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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