Ammonium Hydroxide → HCID 10402610, compound

HRID 1816101Notes

Reaction equation

HRID 1816101 reaction equation
B(Br)(Br)Br.[S:5]1[CH:9]=[CH:8][N:7]=[C:6]1[NH:10][C:11]([C:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22]C)=[CH:19][CH:20]=2)[N:15]([CH:24]([CH3:26])[CH3:25])[CH:14]=1)=[O:12].[OH-].[NH4+]>C(Cl)Cl>[S:5]1[CH:9]=[CH:8][N:7]=[C:6]1[NH:10][C:11]([C:13]1[C:21]2[C:16](=[CH:17][C:18]([OH:22])=[CH:19][CH:20]=2)[N:15]([CH:24]([CH3:26])[CH3:25])[CH:14]=1)=[O:12]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 25134Boron tribromideHCID 10470973HCID 10470973, compound

Product 1

HCID 10402610HCID 10402610, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A 1.0M solution of boron tribromide in methylene chloride (2.70 mL, 2.70 mmol) at 25° C. was treated with a solution of 1-isopropyl-6-methoxy-1H-indole-3-carboxylic acid thiazol-2-ylamide (85 mg, 0.27 mmol) in methylene chloride (2.7 mL). The reaction was stirred at 25° C. for 1 h. At this time, the reaction was cooled to 0° C. and then was treated with a 20% aqueous ammonium hydroxide solution (3 mL). The reaction mixture was stirred at 0° C. for 15 min. At this time, the resulting precipitate was collected by filtration to afford (6-hydroxy-1-isopropyl-1H-indole-3-carboxylic acid thiazol-2-ylamide (31.9 mg, 39%) as a yellow solid: mp 239-241° C.; EI-HRMS m/e calcd for C15H15N3O2S (M) 315.1041, found 315.1039.

Workup

  1. temperatureAt this time, the reaction was cooled to 0° C.
  2. stirringThe reaction mixture was stirred at 0° C. for 15 min
  3. filtrationAt this time, the resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-6277c79245904ca18434833120386333
Source dataset
uspto-grants-2005_04
Patent number
US06881844B2

Reaction notes

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