Water → 2-chloro-N-[6-(2-chloro-2-phenylacetyl)-6H-pyrazolo[4',3':3,4]benzo[1,2-d]thiazol-2-yl]-2-phenylacetamide

HRID 1360839

Reaction equation

HRID 1360839 reaction equation
[S:1]1[C:5]2[C:6]3[CH:12]=[N:11][NH:10][C:7]=3[CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH2:13].[Cl:14][CH:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:16](Cl)=[O:17].C(N([CH2:30][CH3:31])CC)C.[OH2:32]>O1CCCC1>[Cl:14][CH:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:16]([NH:13][C:2]1[S:1][C:5]2[C:6]3[CH:12]=[N:11][N:10]([C:16](=[O:32])[CH:15]([Cl:14])[C:31]4[CH:30]=[CH:21][CH:20]=[CH:19][CH:24]=4)[C:7]=3[CH:8]=[CH:9][C:4]=2[N:3]=1)=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 102902Chloro(phenyl)acetyl chlorideHCID 450776746H-thiazolo[5,4-e]indazol-2-amine

Product 1

HCID 579514352-chloro-N-[6-(2-chloro-2-phenylacetyl)-6H-pyrazolo[4',3':3,4]benzo[1,2-d]thiazol-2-yl]-2-phenylacetamideYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.50 g (2.6 mmol) of 6H-pyrazolo[4′,3′:3,4]benzo[1,2-d]thiazol-2-ylamine and 1.5 g (7.9 mmol) of α-chlorophenylacetyl chloride were dissolved in 10 ml of tetrahydrofuran, and 1.3 g (12.9 mmol) of triethylamine was added dropwise to the mixture under ice-cooling. After the mixture was allowed to warm to room temperature and was stirred overnight, 10 ml of water was added to the mixture to quench the reaction. The reaction mixture was extracted with 20 ml of ethyl acetate twice, dried over 5 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 1.3 g (yield: 100%) of 2-chloro-N-[6-(2-chloro-2-phenylacetyl)-6H-pyrazolo[4′,3′:3,4]benzo[1,2-d]thiazol-2-yl]-2-phenylacetamide.

Workup

  1. temperaturecooling
  2. customto quench
  3. customthe reaction
  4. extractionThe reaction mixture was extracted with 20 ml of ethyl acetate twice
  5. dry with materialdried over 5 g of anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-bccc2275fb4d4150b45000767e7823ce
Source dataset
uspto-grants-2011_02
Patent number
US07879887B2

Linked notes

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