Water → ethyl 3-{2-chloro-5-[1-methyl-1-(4-trifluoromethyl-6H-pyrazolo[4',3':3,4]benzo[1,2-d]thiazol-2-ylcarbamoyl)-ethylamino]-benzoylamino}-propionate

HRID 1360842Notes

Reaction equation

HRID 1360842 reaction equation
Br[C:2]([CH3:23])([CH3:22])[C:3]([NH:5][C:6]1[S:7][C:8]2[C:14]3[CH:15]=[N:16][NH:17][C:13]=3[CH:12]=[C:11]([C:18]([F:21])([F:20])[F:19])[C:9]=2[N:10]=1)=[O:4].[NH2:24][C:25]1[CH:26]=[CH:27][C:28]([Cl:41])=[C:29]([CH:40]=1)[C:30]([NH:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:31].O>C(O)CO>[Cl:41][C:28]1[CH:27]=[CH:26][C:25]([NH:24][C:2]([CH3:23])([C:3](=[O:4])[NH:5][C:6]2[S:7][C:8]3[C:14]4[CH:15]=[N:16][NH:17][C:13]=4[CH:12]=[C:11]([C:18]([F:21])([F:20])[F:19])[C:9]=3[N:10]=2)[CH3:22])=[CH:40][C:29]=1[C:30]([NH:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:31]

Participants

5

Reactant 3

HCID 962WaterHCID 57421781HCID 57421781, compoundHCID 579513762-bromo-2-methyl-N-(4-trifluoromethyl-6H-pyrazolo[4',3':3,4]benzo[1,2-d]thiazol-2-yl)-propionamide

Product 1

HCID 57951397ethyl 3-{2-chloro-5-[1-methyl-1-(4-trifluoromethyl-6H-pyrazolo[4',3':3,4]benzo[1,2-d]thiazol-2-ylcarbamoyl)-ethylamino]-benzoylamino}-propionateYield 13.4%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

0.1 g (0.25 mmol) of 2-bromo-2-methyl-N-(4-trifluoromethyl-6H-pyrazolo[4′,3′:3,4]benzo[1,2-d]thiazol-2-yl)-propionamide and 0.23 g (0.85 mmol) of ethyl 3-(5-amino-2-chlorobenzoylamino)-propionate were heated at 100° C. in 4 ml of ethylene glycol. After the completion of the reaction was confirmed by HPLC, the mixture was cooled to room temperature, and 4 ml of water was added to the mixture. The mixture was extracted with 4 ml of ethyl acetate twice, dried over 3 g of anhydrous magnesium sulfate, and then concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give 20 mg of ethyl 3-{2-chloro-5-[1-methyl-1-(4-trifluoromethyl-6H-pyrazolo[4′,3′:3,4]benzo[1,2-d]thiazol-2-ylcarbamoyl)-ethylamino]-benzoylamino}-propionate.

Workup

  1. extractionThe mixture was extracted with 4 ml of ethyl acetate twice
  2. dry with materialdried over 3 g of anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-2ccd166c5b384829b8ac3020708503b0
Source dataset
uspto-grants-2011_02
Patent number
US07879887B2

Reaction notes

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