2-(4-Methoxyphenyl)butanoic acid → HCID 86676947, compound

HRID 1506818Notes

Reaction equation

HRID 1506818 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:13][CH3:14])[C:10]([OH:12])=O)=[CH:5][CH:4]=1.[NH2:15][C:16]1[S:17][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][N:20]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH2:13][CH3:14])[C:10]([NH:15][C:16]2[S:17][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][N:20]=2)=[O:12])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 346572-(4-Methoxyphenyl)butanoic acidHCID 81531DiisopropylethylamineHCID 3146282-Amino-thiazole-5-carboxylic acid ethyl esterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86676947HCID 86676947, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-methoxyphenyl)butanoic acid (135 mg, 0.70 mmol) and ethyl 2-aminothiazole-5-carboxylate (100 mg, 0.58 mmol) in DMF were added DIEA (112 mg, 0.87 mmol) and HATU (264 mg, 0.70 mmol). The reaction was stirred at room temperature for 4 hrs and partitioned between ethyl acetate and water. The organic layer was dried and concentrated. The residue was purified by biotage column chromatography to afford ethyl 2-(2-(4-methoxyphenyl)butanamido)thiazole-5-carboxylate (163 mg).

Workup

  1. custompartitioned between ethyl acetate and water
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customThe residue was purified by biotage column chromatography

Sources & evidence

ORD record
ord-da29055fae6a4710ad6a8e0b1bde67c2
Source dataset
uspto-grants-2015_12
Patent number
US09221773B2

Reaction notes

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