Hydrochloric Acid → HCID 23143282, compound

HRID 732212Notes

Reaction equation

HRID 732212 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([NH:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:21][C:22]1[CH:41]=[CH:40][C:25]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]([O:38]C)=[O:37])=[CH:30][CH:29]=2)=[CH:24][CH:23]=1.[OH-].[Na+].Cl>CN(C)C=O.CO.O>[CH:1]([C:4]1[N:5]=[C:6]([N:9]([CH2:21][C:22]2[CH:41]=[CH:40][C:25]([CH2:26][O:27][C:28]3[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 23082857Methyl 3-(4-([4-(chloromethyl)benzyl]oxy)phenyl)propanoateHCID 23143256HCID 23143256, compound

Product 1

HCID 23143282HCID 23143282, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-isopropyl-N-(2-pyridin-2-ylethyl)-1,3-thiazole-2-amine (127 mg) in N,N-dimethylformamide (2 mL) was added sodium hydride (20 mg), and the mixture was stirred at room temperature for 1 hr. Methyl 3-{4-([4-(chloromethyl)benzyl]oxy}phenyl)propanoate (159 mg) was added to the reaction mixture at room temperature, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.), and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-1:1 in volume ratio) to give a yellow oil. The oil was dissolved in methanol (5 mL), 2N aqueous sodium hydroxide solution (2 mL) was added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with water, neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was dried using a Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.) and concentrated to give the title compound (105 mg, yield 41%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-1:1 in volume ratio)
  6. customto give a yellow oil
  7. stirringthe mixture was stirred at room temperature for 1 hr
  8. extractionextracted with ethyl acetate
  9. customThe extract was dried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-b3c5b802502c4356b2d6d29862343be8
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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