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

HRID 469108Notes

Reaction equation

HRID 469108 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][NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][N:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)[CH:30]=1.C[Al](C)C>C1COCC1>[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]([N:27]([CH3:26])[CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][N:36]4[CH2:40][CH2:39][CH2:38][CH2:37]4)[CH:30]=3)=[O:22])=[N:18][N:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:25])[CH:4]=1

Participants

5

Reactant 3

HCID 16682925TrimethylaluminumHCID 18525873N-Methyl-3-[(pyrrolidin-1-y)lmethyl]benzylamineHCID 67217606Methyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3,4-oxadiazole-2-carboxylate

Product 1

HCID 583931735-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-N-methyl-N-[3-(pyrrolidin-1-ylmethyl)benzyl]-1,3,4-oxadiazole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to general procedure BK using methyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3,4-oxadiazole-2-carboxylate (150 mg, 0.41 mmol), methyl-(3-pyrrolidin-1-ylmethyl-benzyl)-amine (99 mg, 0.48 mmol), trimethylaluminium (2 M in toluene, 0.44 mL) and THF (15 mL).

Sources & evidence

ORD record
ord-3445413d0b2d48219a34ced8eabc45cf
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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