HCID 59548763, compound → HCID 46945413, compound

HRID 1810978Notes

Reaction equation

HRID 1810978 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:16][C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31](=[O:43])[NH:32][C:33]3[CH:38]=[CH:37][C:36]([S:39]([CH3:42])(=[O:41])=[O:40])=[CH:35][CH:34]=3)[CH2:21][CH2:20]2)=[O:18])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][CH:9]=2)=[O:5])C>O.CO.O1CCOCC1>[Cl:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:16][C:17]([N:19]1[CH2:20][CH2:21][N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31](=[O:43])[NH:32][C:33]3[CH:38]=[CH:37][C:36]([S:39]([CH3:42])(=[O:40])=[O:41])=[CH:35][CH:34]=3)[CH2:23][CH2:24]1)=[O:18])[C:6]([C:4]([OH:5])=[O:3])=[CH:14]2

Participants

3

Reactant 1

HCID 59548763HCID 59548763, compound

Product 1

HCID 46945413HCID 46945413, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 22592949Dioxane methanol waterSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 5-chloro-1-(2-{4-[2-(4-methanesulfonyl-phenylcarbamoyl)-phenyl]-piperazin-1-yl}-2-oxo-ethyl)-1H-indole-2-carboxylic acid ethyl ester (0.14 g, 0.22 mmol) of in a 1:1:1 mixture of water/MeOH/1,4-dioxane (9 mL) is heated at 50° C. for 1 hour during which time all of the solids went into solution. The mixture is cooled to room temperature and concentrated under reduced pressure to remove volatile organics. The pH of the mixture is adjusted to slightly acidic (approx pH 5) by the addition of a 2N solution of hydrochloric acid which caused a solid to precipitate from solution. The formed solid is collected by filtration, washed with water and dried on the filter pad to provide 0.025 g of 5-chloro-1-(2-{4-[2-(4-methanesulfonyl-phenylcarbamoyl)-phenyl]-piperazin-1-yl}-2-oxo-ethyl)-1H-indole-2-carboxylic acid as an off white powder.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customto remove volatile organics
  4. additionThe pH of the mixture is adjusted to slightly acidic (approx pH 5) by the addition of a 2N solution of hydrochloric acid which
  5. customto precipitate from solution
  6. filtrationThe formed solid is collected by filtration
  7. washwashed with water
  8. customdried on the filter pad

Sources & evidence

ORD record
ord-1b1bb544d5b3497b85ffda95dd444d76
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

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