Propionic Acid → HCID 69433339, compound

HRID 1269974Notes

Reaction equation

HRID 1269974 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([NH2:19])[CH2:14]2)=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[N:6][NH:7]2.[C:20](O)(=[O:23])[CH2:21][CH3:22].C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O>[CH3:1][O:2][C:3]1[C:11]([O:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([NH:19][C:20](=[O:23])[CH2:21][CH3:22])[CH2:14]2)=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[N:6][NH:7]2

Participants

8

Reactant 5

HCID 1032Propionic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69429700HCID 69429700, compound

Product 1

HCID 69433339HCID 69433339, compoundYield 116%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under nitrogen, the cis-3-[(4-methoxy-1H-indazol-5-yl)oxy]cyclohexanamine (100 mg, 0.383 mmol) obtained in Example 583 was suspended in N,N-dimethylformamide (2 ml), and propionic acid (31 μl, 0.421 mmol) and triethylamine (107 μl, 0.765 mmol) were added thereto, followed by adding thereto 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide mono-hydrochloride (81 mg, 0.421 mmol) and 1-hydroxybenzotriazole (57 mg, 0.421 mmol). The resulting mixture was stirred at room temperature for 24 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate (three times). The combined ethyl acetate layer was washed with a saturated aqueous sodium chloride solution, dried by the addition of anhydrous magnesium sulfate, and then filtered. The solvent was distilled off under reduced pressure and the resulting concentration residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=100/0, 100/2) to obtain N-[cis-3-[(4-methoxy-1H-indazol-5-yl)oxy]cyclohexyl]propanamide (141 mg, yield 116%) as light-yellow tar.

Workup

  1. additionby adding
  2. extractionfollowed by extraction with ethyl acetate (three times)
  3. washThe combined ethyl acetate layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried by the addition of anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationThe solvent was distilled off under reduced pressure
  7. concentrationthe resulting concentration residue
  8. customwas purified by a silica gel column chromatography (eluent: chloroform/methanol=100/0, 100/2)

Sources & evidence

ORD record
ord-5bc291121ebb4bd2b7cf483acbf5d4d1
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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