3,3-Dimethylbutylamine → HCID 18794535, compound

HRID 1004443Notes

Reaction equation

HRID 1004443 reaction equation
C(Cl)(=O)C(Cl)=O.Cl.C1(C2C=CC=CC=2)C=CC=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[CH:26]=[CH:25][C:24]2[C:23](=[O:27])[CH:22](CCN3CCC(C4C=CC=CC=4)CC3)[CH2:21][CH2:20][C:19]=2[CH:18]=1)=[O:16].[CH3:48][C:49](C)([CH3:53])[CH2:50]CN.C(Cl)Cl.O>C1(C)C=CC=CC=1.CN(C=O)C>[CH3:48][C:49]([CH3:53])([CH3:50])[CH2:10][CH2:9][NH:14][C:15]([C:17]1[CH:26]=[CH:25][C:24]2[C:23](=[O:27])[CH2:22][CH2:21][CH2:20][C:19]=2[CH:18]=1)=[O:16]

Participants

7

Reactant 4

HCID 197093,3-DimethylbutylamineHCID 65578Oxalyl chlorideHCID 21908982Water methylene chlorideHCID 131721763HCID 131721763, compound

Product 1

HCID 18794535HCID 18794535, compoundYield 119.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

Oxalyl chloride (2M in CH2Cl2, 4.3 mL, 8.6 mmol) was added to a stirring suspension of acid 2 (0.90 g, 4.3 mmol) in toluene (20 mL). DMF (1 drop) was added and the reaction began bubbling. After 2 hours, the reaction was evaporated in vacuo. The residue was dissolved in CH2Cl2 (21 mL) and 3,3-dimethylbutylamine (0.87 g, 1.2 mL, 8.6 mmol) was added. After stirring at ambient temperature for 4 hours, the reaction was transferred to a separatory funnel with CH2Cl2 /H2O. Extraction with CH2Cl2 (3×30 mL) and drying over MgSO4 afforded 1.4 g of product after evaporation of the solvent. Flash chromatography (silica gel, 37 mm dia, 40% EtOAc/hexane) afforded 1.2 g of product. Recrystallization from EtOAc/hexane (10 mL/10 mL) afforded 0.89 g (75%) of pure crystalline title compound.

Workup

  1. customthe reaction began bubbling
  2. customthe reaction was evaporated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (21 mL)
  4. extractionExtraction with CH2Cl2 (3×30 mL)
  5. dry with materialdrying over MgSO4

Sources & evidence

ORD record
ord-7d5e4ac2927b4049a99ee568bd071a6d
Source dataset
uspto-grants-2000_04
Patent number
US06048877

Reaction notes

Loading…