1-(2-pyrrolidin-1-ylethyl)piperazine → 4-Methoxy-N,2,6-trimethyl-N-[(5-{[4-(2-pyrrolidin-1-ylethyl)piperazin-1-yl]carbonyl}-1,3,4-thiadiazol-2-yl)methyl]benzenesulfonamide

HRID 469126

Reaction equation

HRID 469126 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[S:20][C:19]([C:21]([O:23]C)=O)=[N:18][N:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:25])[CH:4]=1.[N:26]1([CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH2:30][CH2:29][CH2:28][CH2:27]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]([CH3:14])[CH2:15][C:16]2[S:20][C:19]([C:21]([N:36]3[CH2:35][CH2:34][N:33]([CH2:32][CH2:31][N:26]4[CH2:27][CH2:28][CH2:29][CH2:30]4)[CH2:38][CH2:37]3)=[O:23])=[N:18][N:17]=2)(=[O:11])=[O:12])=[C:5]([CH3:25])[CH:4]=1

Participants

5

Reactant 3

HCID 27372501-(2-pyrrolidin-1-ylethyl)piperazineHCID 16682925TrimethylaluminumHCID 58392977Methyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3,4-thiadiazole-2-carboxylate

Product 1

HCID 583930354-Methoxy-N,2,6-trimethyl-N-[(5-{[4-(2-pyrrolidin-1-ylethyl)piperazin-1-yl]carbonyl}-1,3,4-thiadiazol-2-yl)methyl]benzenesulfonamide

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-thiadiazole-2-carboxylate (125 mg, 0.32 mmol), 1-(2-pyrrolidin-1-yl-ethyl)-piperazine (71 mg, 0.39 mmol), trimethylaluminium (2 M in toluene, 0.35 mL) and THF (10 mL).

Sources & evidence

ORD record
ord-c43ff1f150fd4482ad99783171323ffd
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Linked notes

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