Propylamine → HCID 22339194, compound

HRID 585384Notes

Reaction equation

HRID 585384 reaction equation
C[C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][C:38]=1[CH3:39])[C:5]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]([N:17]2[C:26]3[C:21](=[CH:22][C:23]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32](O)=[O:33])=[CH:24][CH:25]=3)[CH2:20][CH2:19][CH2:18]2)[CH2:9][CH:8]1[CH3:35])=[O:6].O[N:41]1[C:45]2C=CC=[CH:49][C:44]=2N=N1.Cl.[CH2:51](N=C=NCCCN(C)C)C.C(N)CC.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:35][CH:8]1[CH2:9][CH:10]([N:17]2[C:26]3[C:21](=[CH:22][C:23]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([NH:41][CH2:45][CH2:44][CH3:49])=[O:33])=[CH:24][CH:25]=3)[CH2:20][CH2:19][CH2:18]2)[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]1[C:5](=[O:6])[C:4]1[CH:36]=[CH:37][C:38]([CH3:39])=[C:2]([CH3:51])[CH:3]=1

Participants

7

Reactant 5

HCID 7852PropylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22339198HCID 22339198, compound

Product 1

HCID 22339194HCID 22339194, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-[[1-[1-(3,4-Dimethylbenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]-1,2,3,4-tetrahydro-6-quinolinyl]oxy]pentanoic acid (0.20 g, 0.37 mmol) prepared in Example 164 and 1-hydroxybenzotriazole (50 mg, 0.37 mmol) were dissolved in N,N-dimethylformamide (3 ml). To this solution, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) (92 mg, 0.48 mmol) was added and the resulting mixture was stirred at room temperature for 10 minutes. After addition of propylamine (91 μl), the mixture was stirred at room temperature for an additional 15 hours. Aqueous sodium bicarbonate was added to the reaction mixture, which was then extracted with ethyl acetate. The extracted solution was washed with water and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1 to 4:1) to give the titled compound (0.14 g, yield: 68%) as an amorphous powder. (cis:trans=3:2)

Workup

  1. stirringthe mixture was stirred at room temperature for an additional 15 hours
  2. extractionwas then extracted with ethyl acetate
  3. washThe extracted solution was washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1 to 4:1)

Sources & evidence

ORD record
ord-21eb4a53051f44ea80d16681b5b933d1
Source dataset
uspto-grants-2005_08
Patent number
US06930104B2

Reaction notes

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