Dimethylamine → HCID 86176840, compound

HRID 716071Notes

Reaction equation

HRID 716071 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:8](=[O:9])[CH2:7][S:6][C:5]1=[O:10].[CH3:11][NH:12][CH3:13].O>CN(C=O)C>[CH3:11][N:12]([CH3:13])[CH2:2][CH2:3][N:4]1[C:8](=[O:9])[CH2:7][S:6][C:5]1=[O:10]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 16392506HCID 16392506, compound

Product 1

HCID 86176840HCID 86176840, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a 35 ml seal tube, 3-(2-bromoethyl)thiazolidine-2,4-dione (1.5 g, 0.6.69 mmole) was taken in DMF (1 mL) under N2 atmosphere and dimethyl amine (2M solution in THF) (11 mL, 20.0 mmole) was added. The reaction mixture was heated to 50° C. for 16 hrs. After completion of the reaction, water was added to the reaction mixture and product was extracted with ethyl acetate. The combined organic layer was dried over Na2SO4 and evaporated to get the crude product which was purified using column purification using 60-120 mesh size neutral silica by eluting the compound with 2% MeOH in CH2Cl2 to yield 0.3 g of 3-(2-(dimethylamino)ethyl)thiazolidine-2,4-dione which was converted to 3-(2-(dimethylamino)-ethyl)-5-(4-(7-pivaloyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzylidene)-thiazolidine-2,4-dione as described in Example 6 above.

Workup

  1. customTo a 35 ml seal tube
  2. additionwas added to the reaction mixture and product
  3. extractionwas extracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. customevaporated
  6. customto get the crude product which
  7. customwas purified
  8. customcolumn purification
  9. washby eluting the compound with 2% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-a65ddb829fd647f0b70da1002462ce52
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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