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

HRID 469127

Reaction equation

HRID 469127 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][CH2:33][N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH2:30][CH2:29][CH2:28][CH2:27]1.C[Al](C)C>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:25])[C:6]([S:10]([N:13]([CH3:14])[CH2:15][C:16]2[S:20][C:19]([C:21]([N:37]3[CH2:36][CH2:35][N:34]([CH2:33][CH2:32][CH2:31][N:26]4[CH2:27][CH2:28][CH2:29][CH2:30]4)[CH2:39][CH2:38]3)=[O:23])=[N:18][N:17]=2)(=[O:12])=[O:11])=[C:7]([CH3:9])[CH:8]=1

Participants

5

Reactant 3

HCID 27372521-(3-Pyrrolidinopropyl)PiperazineHCID 16682925TrimethylaluminumHCID 58392977Methyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3,4-thiadiazole-2-carboxylate

Product 1

HCID 461752094-Methoxy-N,2,6-trimethyl-N-[(5-{[4-(3-pyrrolidin-1-ylpropyl)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 (200 mg, 0.50 mmol), 1-(3-pyrrolidin-1-ylpropyl)piperazine (118 mg, 0.60 mmol), THF (10 mL) and trimethylaluminium (2.0 M in toluene, 0.55 mL). The crude product was purified by FCC, eluting with 0-2% MeOH in DCM to afford the title compound as a white solid.

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified by FCC
  3. washeluting with 0-2% MeOH in DCM

Sources & evidence

ORD record
ord-0b9f8f485709411d8e27f24bb04e2a7e
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Linked notes

Loading…