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

HRID 469101Notes

Reaction equation

HRID 469101 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[CH2:32][CH2:31][N:30]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([CH2:40][NH:41][CH3:42])=[CH:36][CH:35]=2)[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:41]([CH2:40][C:37]3[CH:36]=[CH:35][C:34]([CH2:33][N:30]4[CH2:31][CH2:32][CH:28]([O:27][CH3:26])[CH2:29]4)=[CH:39][CH:38]=3)[CH3:42])=[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 583931511-{4-[(3-methoxypyrrolidin-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 461761555-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-N-{4-[(3-methoxypyrrolidin-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-[(3-methoxypyrrolidin-1-yl)methyl]phenyl}-N-methylmethanamine (45 mg, 0.19 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. The fraction collected was dissolved in DCM (5 mL) and shaken with PL-MIA resin for 2 h, and the beads were filtered and washed with DCM (10 mL). The combined filtrates were concentrated in vacuo and the residue 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. customThe fraction collected
  5. dissolutionwas dissolved in DCM (5 mL)
  6. filtrationthe beads were filtered
  7. washwashed with DCM (10 mL)
  8. concentrationThe combined filtrates were concentrated in vacuo
  9. customthe residue purified

Sources & evidence

ORD record
ord-712960896b2c4424a32079096c3c886b
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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