Toluene → HCID 46175825, compound

HRID 469087Notes

Reaction equation

HRID 469087 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH2:17][C:18]2[O:22][C:21]([C:23]([O:25]CC)=O)=[N:20][CH:19]=2)[CH:14]2[CH2:16][CH2:15]2)(=[O:12])=[O:11])=[C:5]([CH3:28])[CH:4]=1.[CH3:29][N:30]1[CH2:35][CH2:34][CH:33]([CH2:36][N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH2:32][CH2:31]1.C[Al](C)C.C1(C)C=CC=CC=1>ClCCCl>[CH:14]1([N:13]([CH2:17][C:18]2[O:22][C:21]([C:23]([N:40]3[CH2:39][CH2:38][N:37]([CH2:36][CH:33]4[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]4)[CH2:42][CH2:41]3)=[O:25])=[N:20][CH:19]=2)[S:10]([C:6]2[C:7]([CH3:9])=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH3:28])(=[O:11])=[O:12])[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 27369421-((1-Methyl-4-piperidinyl)methyl)piperazineHCID 16682925TrimethylaluminumHCID 58393056HCID 58393056, compound

Product 1

HCID 46175825HCID 46175825, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of ethyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](cyclopropyl)amino}methyl)-1,3-oxazole-2-carboxylate (25 mg, 0.07 mmol) and 1-(N-methylpiperidin-4-yl-methyl)piperazine (26 mg, 0.13 mmol) in DCE (1 mL) was added trimethylaluminium 2M in toluene (65 μL, 0.13 mmol) and the mixture stirred at 60° C. for 1.5 h. The reaction mixture was washed with saturated aqueous NaHCO3 and extracted with DCM. The organic extract was dried over MgSO4, and concentrated in vacuo. The residue was purified by FCC eluting with 95:4.5:0.5 NH3/MeOH/DCM. This afforded the title compound as a colourless oil.

Workup

  1. washThe reaction mixture was washed with saturated aqueous NaHCO3
  2. extractionextracted with DCM
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by FCC
  7. washeluting with 95:4.5:0.5 NH3/MeOH/DCM

Sources & evidence

ORD record
ord-d43364fa6a7443c1a4475a1c433b1a7a
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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