HCID 18368038, compound → HCID 18368014, compound

HRID 379832Notes

Reaction equation

HRID 379832 reaction equation
C([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15](=[O:25])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([OH:24])=[O:23])[CH:17]=1)(=O)C.Cl.[CH3:27]O>>[NH2:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15](=[O:25])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([O:24][CH3:27])=[O:23])[CH:17]=1

Participants

3

Reactant 2

HCID 18368038HCID 18368038, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 18368014HCID 18368014, compound

Conditions

Temperature
60 °C

Procedure

A mixture of 3-acetylamino-6-chloro-2-(3-carboxybenzoyl)indole (Example 132, 0.9 g, 2.5 mmol) and 10% HCl—MeOH (30 ml) was heated at 60° C. for 8 h. The mixture was cooled and concentrated, and the residue partitioned between water (100 ml) and ethyl acetate (100 ml). The organic layer was separated and washed with brine (50 ml), and dried (MgSO4) and solvent removed by evaporation. The residual solid was purified by flash column chromatography eluting with hexane/ethyl acetate (2/1) to afford 0.5 g of a title compound as a yellow solid. m.p.: 187-189° C. (ethyl acetate/hexane) 1H-NMR (DMSO-d6) δ: 9.14 (1H, br s), 8.47 (1H, dd, J=1.8, 1.1 Hz), 8.20 (1H, ddd, J=7.7, 1.8, 1.1 Hz), 8.03 (1H, ddd, J=7.7, 1.8, 1.1 Hz), 7.69-7.58 (2H, m), 7.28 (1H, d, J=1.8 Hz), 6.97 (1H, dd, J=1.4, 8.4 Hz), 6.04 (2H, br s), 3.95 (3H, s)

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. customthe residue partitioned between water (100 ml) and ethyl acetate (100 ml)
  4. customThe organic layer was separated
  5. washwashed with brine (50 ml)
  6. dry with materialdried (MgSO4) and solvent
  7. customremoved by evaporation
  8. customThe residual solid was purified by flash column chromatography
  9. washeluting with hexane/ethyl acetate (2/1)

Sources & evidence

ORD record
ord-d4adb608a3144c429e699a14661d7b23
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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