Pyridine → HCID 19973188, compound

HRID 327846Notes

Reaction equation

HRID 327846 reaction equation
O.Br.[NH2:3][CH2:4][C:5]([NH:7][N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13](=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20])=[O:6].N[CH2:23][C:24](NN1C=CC=C1C(=O)C1C=CC=CC=1F)=[O:25].Br.N1C=CC=CC=1.C(OC(=O)C)(=O)C>CN(C)C=O.C(Cl)Cl.O>[C:24]([NH:3][CH2:4][C:5]([NH:7][N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13](=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20])=[O:6])(=[O:25])[CH3:23]

Participants

7

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 70341925HCID 70341925, compound

Product 1

HCID 19973188HCID 19973188, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-N-[2-(2-fluorobenzoyl)-1H-pyrrol-1-yl]acetamide hydrobromide hemihydrate (2.09 g) in 10 ml of anhydrous dimethylformamide and 40 ml of anhydrous DCM were added pyridine (1.89 g) and acetic anhydride (1.22 g). The reaction mixture was stirred at room temperature for 1 hour, subsequently diluted with water and extracted with DCM. The combined organic layers were washed with 5% hydrochloric acid and water, dried over magnesium sulfate and evaporated in vacuo. The residual oil was recrystallized from DCM/ethyl ether affording the product as crystals (1.58 g), m.p. 146°-147° C.

Workup

  1. extractionextracted with DCM
  2. washThe combined organic layers were washed with 5% hydrochloric acid and water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residual oil was recrystallized from DCM/ethyl ether affording the product as crystals (1.58 g), m.p. 146°-147° C.

Sources & evidence

ORD record
ord-79e1a04bc0f545d3b1435ce7bc4dfac5
Source dataset
uspto-grants-1993_12
Patent number
US05274116

Reaction notes

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