Diisopropylethylamine → HCID 71668098, compound

HRID 1507439Notes

Reaction equation

HRID 1507439 reaction equation
[OH:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:20])[C:7]([CH3:19])=[C:8]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[O:9]2)=[CH:4][CH:3]=1.[F:21][C:22]([F:28])([F:27])[CH2:23][C:24](O)=[O:25].Cl.C(N=C=NCCCN(C)C)C.C(N(C(C)C)CC)(C)C>CN(C)C=O>[OH:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:20])[C:7]([CH3:19])=[C:8]([CH:13]3[CH2:18][CH2:17][N:16]([C:24](=[O:25])[CH2:23][C:22]([F:28])([F:27])[F:21])[CH2:15][CH2:14]3)[O:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27779723,3,3-Trifluoropropionic acidHCID 117701633HCID 117701633, compound

Product 1

HCID 71668098HCID 71668098, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-hydroxy-3,8-dimethyl-2-(piperidin-4-yl)-4H-chromen-4-one (68 mg, 0.25 mmol) obtained in Example 7-2, 3,3,3-trifluoropropionic acid (33 μL, 0.30 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (192 mg, 1.00 mmol), and diisopropylethylamine (86 μL, 0.50 mmol) in dimethylformamide (1.5 mL) was stirred at room temperature for 4 hours. The reaction solution was concentrated, and water was added to the obtained residue, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate. The desiccant was filtered off, and then the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0→95/5) to obtain 13 mg of the title compound (yield: 13%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionwater was added to the obtained residue
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationThe desiccant was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0→95/5)

Sources & evidence

ORD record
ord-18e863f3e50940b9a9caaff2a01e4fe0
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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