Pyridine → HCID 18367825, compound

HRID 379905Notes

Reaction equation

HRID 379905 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:3]=1[C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[NH:15][C:16](=[O:19])[CH2:17][CH3:18])=[CH:12][CH:11]=[C:10]([Cl:20])[CH:9]=2)=[O:5].N1C=CC=CC=1.[C:32](Cl)(=[O:34])[CH3:33]>ClCCl>[C:32]([NH:1][C:2]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:3]=1[C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[NH:15][C:16](=[O:19])[CH2:17][CH3:18])=[CH:12][CH:11]=[C:10]([Cl:20])[CH:9]=2)=[O:5])(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 18367903HCID 18367903, compound

Product 1

HCID 18367825HCID 18367825, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-amino-5-chlorobenzoyl)-6-chloro-3-(propionylamino)indole (Example 389, 217 mg, 0.576 mmol) and pyridine (0.12 ml, 1.50 mmol) in dichloromethane (10 ml) was added acetyl chloride (53 μl, 0.749 mmol) at 0° C. After stirring at room temperature for 1 h, the mixture was concentrated and the residue was diluted with ethyl acetate (100 ml). The solution was washed with 2N aqueous HCl (30 ml×2), saturated aqueous sodium bicarbonate (30 ml), and dried (MgSO4). Removal of solvent gave a crystalline residue. Recrystallization from ethyl acetate gave 163 mg (68%) of the title compound. m.p.: 264-266° C. IR (KBr) ν: 3260, 1676, 1655, 1578, 1547, 1508, 1313, 1234, 1205, 1006, 918, 841 cm−1

Workup

  1. concentrationthe mixture was concentrated
  2. additionthe residue was diluted with ethyl acetate (100 ml)
  3. washThe solution was washed with 2N aqueous HCl (30 ml×2), saturated aqueous sodium bicarbonate (30 ml)
  4. dry with materialdried (MgSO4)
  5. customRemoval of solvent
  6. customgave a crystalline residue
  7. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-24146d93432c42308b09d0ff28e52bbe
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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