Trimethylaluminum → Ammonia

HRID 469100Notes

Reaction equation

HRID 469100 reaction equation
[CH:1]1([N:4]([CH2:18][C:19]2[O:23][C:22]([C:24]([O:26]CC)=O)=[N:21][N:20]=2)[S:5]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=2[CH3:17])(=[O:7])=[O:6])[CH2:3][CH2:2]1.[CH3:29][NH:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][N:39]2[CH2:43][CH2:42][CH2:41][CH2:40]2)=[CH:34][CH:33]=1.C[Al](C)C>ClCCCl>[NH3:4].[CH:1]1([N:4]([CH2:18][C:19]2[O:23][C:22]([C:24]([N:30]([CH3:29])[CH2:31][C:32]3[CH:33]=[CH:34][C:35]([CH2:38][N:39]4[CH2:43][CH2:42][CH2:41][CH2:40]4)=[CH:36][CH:37]=3)=[O:26])=[N:21][N:20]=2)[S:5]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=2[CH3:17])(=[O:6])=[O:7])[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 16682925TrimethylaluminumHCID 18525869N-Methyl-4-(pyrrolidin-1-ylmethyl)benzylamineHCID 58393194Ethyl 5-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3,4-oxadiazole-2-carboxylate

Product 2

HCID 222AmmoniaHCID 461761545-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-N-methyl-N-[4-(pyrrolidin-1-ylmethyl)benzyl]-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 Ethyl 5-({cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3,4-oxadiazole-2-carboxylate (30 mg, 0.07 mmol), N-methyl-1-[4-(pyrrolidin-1-ylmethyl)phenyl]methanamine (30 mg, 0.15 mmol) and trimethylaluminium (2 M in toluene, 0.07 mL) in DCE (5 mL). The crude product was purified twice using FCC, eluting with 95:4.5:0.5, then 98:1:0.5 DCM:MeOH:NH3, to afford the title compound.

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified twice using FCC
  3. washeluting with 95:4.5:0.5

Sources & evidence

ORD record
ord-6381cec9e4984513948c1694a0b6132e
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

Loading…