Diethyl Ether → HCID 69607348, compound

HRID 1244139Notes

Reaction equation

HRID 1244139 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[C:9]([Cl:18])[S:8][C:7]=1[NH:19][C:20](=[O:24])[CH2:21][C:22]#[N:23])=[O:5])[CH3:2].[C:25]([O-])(O)=O.[Na+].[CH2:30](Br)[CH:31]=[CH2:32].CCO[CH2:37][CH3:38]>CN(C=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:12]=[CH:13][C:14]([N:17]([CH2:25][CH:37]=[CH2:38])[CH2:30][CH:31]=[CH2:32])=[CH:15][CH:16]=2)=[C:9]([Cl:18])[S:8][C:7]=1[NH:19][C:20](=[O:24])[CH2:21][C:22]#[N:23])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7841Allyl bromideHCID 516892Sodium BicarbonateHCID 69607391HCID 69607391, compound

Product 1

HCID 69607348HCID 69607348, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

An ambient mixture of 2-(2-cyano-acetylamino)-4-(4-aminophenyl)-5-chloro-thiophene-3-carboxylic acid ethyl ester (365 mg, 1.00 mmol), NaHCO3 (210 mg, 2.50 mmol), and allyl bromide (0.173 mL, 2.00 mmol) in DMF (3.5 mL) was stirred for 18 h. The reaction was then diluted with H2O (5 mL) and Et2O (5 mL). The layers were separated, and the aqueous was extracted with additional Et2O (2×5 mL). The combined organic layers were dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure to an oil that was used without further purification. MS (ESI) m/e 442 (M−H)−.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous was extracted with additional Et2O (2×5 mL)
  3. dry with materialThe combined organic layers were dried with anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to an oil that
  6. customwas used without further purification

Sources & evidence

ORD record
ord-996e8eed09804ea99a7db888df3ca3d9
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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