Water → (1-Amino-1H-pyrrol-2-yl)-(3-methyl-2-thienyl)methanone

HRID 327838Notes

Reaction equation

HRID 327838 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([C:9]1[N:10]([N:14]2C(=O)C3C(=CC=CC=3)C2=O)[CH:11]=[CH:12][CH:13]=1)=[O:8].CN.O.C(OCC)(=O)C>CN(C=O)C>[NH2:14][N:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[C:7]([C:3]1[S:4][CH:5]=[CH:6][C:2]=1[CH3:1])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 8857Ethyl AcetateHCID 199731602-[(3-Methyl-2-thienyl)carbonyl-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)dion

Product 1

HCID 19973163(1-Amino-1H-pyrrol-2-yl)-(3-methyl-2-thienyl)methanoneYield 79.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution consisting of 2-[2-[(3-methyl-2-thienyl)carbonyl]-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)dione (11.5 g) in DMF (30 ml) was added 40% methylamine (aq., 34.0 ml) solution at room temperature. The reaction mixture was stirred at ambient temperature for 3.5 hours, then poured into water and ethyl acetate. The layers were separated and the aqueous phase was extracted thrice with EtOAc. The combined organics were washed with water, brine, and dried (MgSO4). Filtration and concentration gave the crude product. Purification via preparative HPLC (silica gel, 2:1 heptane/EtOAc), followed by crystallization from ether/pentane afforded 5.6 g of the product as a solid, m.p. 42°-44° C.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted thrice with EtOAc
  3. washThe combined organics were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and concentration
  6. customgave the crude product
  7. customPurification via preparative HPLC (silica gel, 2:1 heptane/EtOAc)
  8. customfollowed by crystallization from ether/pentane

Sources & evidence

ORD record
ord-d0a5a95303c1443ba7ca6f8a72dd4f4a
Source dataset
uspto-grants-1993_12
Patent number
US05274116

Reaction notes

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