Propionic Acid → HCID 178460281, compound

HRID 1269964Notes

Reaction equation

HRID 1269964 reaction equation
C(N(CC)CC)C.[C:8]([OH:12])(=O)[CH2:9][CH3:10].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH3:35][C:36]1[C:44]([O:45][C@@H:46]2[CH2:51][CH2:50][C@H:49]([NH2:52])[CH2:48][CH2:47]2)=[CH:43][C:42]([CH3:53])=[C:41]2[C:37]=1[CH:38]=[N:39][NH:40]2>CN(C)C=O>[CH3:35][C:36]1[C:44]([O:45][C@@H:46]2[CH2:51][CH2:50][C@H:49]([NH:52][C:8](=[O:12])[CH2:9][CH3:10])[CH2:48][CH2:47]2)=[CH:43][C:42]([CH3:53])=[C:41]2[C:37]=1[CH:38]=[N:39][NH:40]2

Participants

7

Reactant 5

HCID 1032Propionic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178431638HCID 178431638, compound

Product 1

HCID 178460281HCID 178460281, compoundYield 110.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (108 μl, 0.775 mmol), propionic acid (32 μl, 0.429 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (83 mg, 0.433 mmol) and 1-hydroxybenzotriazole (58 mg, 0.429 mmol) were added in that order to a dimethylformamide solution (2 ml) of the cis-4-[(4,7-dimethyl-1H-indazol-5-yl)oxy]cyclohexanamine (100 mg, 0.386 mmol) obtained in Example 658, and the resulting mixture was stirred at room temperature for 20 hours. The reaction was terminated by the addition of water, followed by extraction with ethyl acetate-toluene (1:1). The extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent, whereby a crude product was obtained. The crude product was purified by a silica gel chromatography (eluent: chloroform/methanol=100:2) to obtain cis-N-{4-[(4,7-dimethyl-1H-indazol-5-yl)oxy]cyclohexyl}propanamide (134 mg, 100%).

Workup

  1. customThe reaction was terminated by the addition of water
  2. extractionfollowed by extraction with ethyl acetate-toluene (1:1)
  3. washThe extract solution was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent, whereby a crude product
  7. customwas obtained
  8. customThe crude product was purified by a silica gel chromatography (eluent: chloroform/methanol=100:2)

Sources & evidence

ORD record
ord-49c28b9a18954259b7e6b2a5cc93d2ba
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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