Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | HCID 16392506 | HCID 16392506 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86176840 | HCID 86176840 | 23.8% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09187487B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-a65ddb829fd647f0b70da1002462ce52 |
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| Source note | uspto-grants-2015_11 |
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