Trimethylaluminum → 5-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-N-{4-[(4-methoxypiperidin-1-yl)methyl]benzyl}-N-methyl-1,3,4-oxadiazole-2-carboxamide

HRID 469102Notes

Reaction equation

HRID 469102 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](OC)=[O:22])=[N:18][N:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:25])[CH:4]=1.[CH3:26][O:27][CH:28]1[CH2:33][CH2:32][N:31]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([CH2:41][NH:42][CH3:43])=[CH:37][CH:36]=2)[CH2:30][CH2:29]1.C[Al](C)C>ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:25])[C:6]([S:10]([N:13]([CH2:15][C:16]2[O:20][C:19]([C:21]([N:42]([CH2:41][C:38]3[CH:37]=[CH:36][C:35]([CH2:34][N:31]4[CH2:32][CH2:33][CH:28]([O:27][CH3:26])[CH2:29][CH2:30]4)=[CH:40][CH:39]=3)[CH3:43])=[O:22])=[N:18][N:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:7]([CH3:9])[CH:8]=1

Participants

5

Reactant 3

HCID 16682925TrimethylaluminumHCID 583931801-{4-[(4-methoxypiperidin-1-yl)methyl]phenyl}-N-methylmethanamineHCID 67217606Methyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3,4-oxadiazole-2-carboxylate

Product 1

HCID 583934165-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-N-{4-[(4-methoxypiperidin-1-yl)methyl]benzyl}-N-methyl-1,3,4-oxadiazole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The title compound was prepared according to general procedure AT using methyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3,4-oxadiazole-2-carboxylate (30 mg, 0.08 mmol), 1-{4-[(4-methoxypiperidin-1-yl)methyl]phenyl}-N-methylmethanamine (35 mg, 0.14 mmol) and trimethylaluminium (2 M in toluene, 0.08 mL) in DCE (5 mL). The crude product was purified using FCC, eluting with 95:4.5:0.5 DCM:MeOH:NH3. A portion of the fraction collected was further purified using prep method D to afford the title compound.

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified
  3. washeluting with 95:4.5:0.5 DCM
  4. customA portion of the fraction collected
  5. customwas further purified

Sources & evidence

ORD record
ord-3855756f53a54a85955bdc5ef11edc36
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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