Pyridine → HCID 2807639, compound

HRID 2228565Notes

Reaction equation

HRID 2228565 reaction equation
C[C:2]1[C:3]([NH2:10])=[C:4]([C:7]([OH:9])=[O:8])[S:5][CH:6]=1.N1C=CC=C[CH:12]=1.[C:17]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl>[C:17]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH:10][C:3]2[CH:2]=[CH:6][S:5][C:4]=2[C:7]([O:9][CH3:12])=[O:8])=[O:26])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 743724-tert-Butylbenzoyl chlorideHCID 149896783-Amino-4-methylthiophene-2-carboxylic acid

Product 1

HCID 2807639HCID 2807639, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl 3-aminothiophene-2-carboxylic acid (5.0 g, 35.0 mmol), pyridine(2.82 mL, 35.0 mmol), and dry methylene chloride (160 mL) at 0 C was added 4-tert-butylbenzoyl chloride(6.21 mL, 31.8 mmol) and stirred for 1 h. The reaction was concentrated, dissolved in ethyl acetate, washed with water (4×) and brine, MgSO4 dried and concentrated. The residue was chromatographed (2% ethyl acetate/hexanes to 5% ethyl acetate/hexanes) to afford the title compound as a solid (9.67 g, 96% yield); NMR(CDCl3) δ1.36(s, 9H), 3.93(s, 3H), 7.54(d, J=8.4 Hz, 2H), 7.54(d, J=5.4 Hz, 1H), 7.95(d, J=8.4 Hz, 2H), 8.30(d, J=5.4 Hz, 1H), 11.16(s, 1H); MS(FD): 317.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with water (4×) and brine, MgSO4
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was chromatographed (2% ethyl acetate/hexanes to 5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-234db8977af8419fb044e98eac34d7df
Source dataset
uspto-grants-2002_07
Patent number
US06417200B1

Reaction notes

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