Hydrochloric Acid → HCID 69428801, compound

HRID 1295288Notes

Reaction equation

HRID 1295288 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[H-].[Na+].Cl[CH2:23][C:24]1[CH:43]=[CH:42][C:27]([O:28][CH2:29][C:30]2[N:31]=[C:32]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[O:33][C:34]=2[CH3:35])=[CH:26][CH:25]=1.Cl>CN(C)C=O>[CH3:1][N:2]([C:3]1[S:4][C:5]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1)[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:28][CH2:29][C:30]2[N:31]=[C:32]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[O:33][C:34]=2[CH3:35])=[CH:42][CH:43]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazoleHCID 22930677HCID 22930677, compound

Product 1

HCID 69428801HCID 69428801, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-[2-(N-methylamino)-4-phenyl-5-thiazolyl]propionate (400 mg) in N,N-dimethylformamide (10 ml) was added sodium hydride (60% in oil, 70 mg) at 0° C. and the mixture was stirred at said temperature for 10 min. 4-(4-Chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (500 mg) was added and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into ice water, neutralized with 2N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and methyl 3-[2-[N-methyl-N-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]amino]-4-phenyl-5-thiazolyl]propionate (580 mg, yield 72%) was obtained as a colorless oil from fraction eluted with ethyl acetate-hexane (1:9, volume ratio).

Workup

  1. customfor 10 min
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e400fa10d47d4d89992004e426e761f8
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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