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

HRID 1080466Notes

Reaction equation

HRID 1080466 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-02a7d9c5fc0a4e7dafc88c6631662d51
Source dataset
uspto-grants-1996_12
Patent number
US05580987

Reaction notes

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