Diisopropylethylamine → HCID 22632190, compound

HRID 2416728Notes

Reaction equation

HRID 2416728 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:23]=[CH:22][C:9]2[CH2:10][CH:11]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:12](=[O:16])[N:13]([CH3:15])[CH2:14][C:8]=2[CH:7]=1.CS[C:26]1[NH:27][CH2:28][CH2:29][N:30]=1.C(N(C(C)C)CC)(C)C>CC(N(C)C)=O>[NH:30]1[CH2:29][CH2:28][N:27]=[C:26]1[NH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:23]=[CH:22][C:9]2[CH2:10][CH:11]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:12](=[O:16])[N:13]([CH3:15])[CH2:14][C:8]=2[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 883692-Methylthio-2-imidazoline hydroiodideHCID 54417205HCID 54417205, compound

Product 1

HCID 22632190HCID 22632190, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl (±)-8-[3-amino-1-propyloxy]-2-methyl-3-oxo-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (0.3 g, 1 mmol), 2-methylthioimidazoline (0.46 g, 2 mmol), diisopropylethylamine (0.42 mL, 2 mmol) and dimethylacetamide (3 mL) was heated to 100° C. under argon. After 2 hr, the reaction was concentrated under vacuum and the residue was partitioned between CHCl3 and H2O. The organic phase was dried (MgSO4) and concentrated, and the residue was purified by preparative HPLC to give the title compound (0.24 g, 51%) as a yellow oil: MS (ES) m/e 389.4 (M+H)+.

Workup

  1. concentrationthe reaction was concentrated under vacuum
  2. customthe residue was partitioned between CHCl3 and H2O
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-4a34a1314f0b445ea2289f7e7f7ac9e4
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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