Triethylamine → HCID 68494892, compound

HRID 444729Notes

Reaction equation

HRID 444729 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=2)[C:9](O)=[O:10])=[CH:4][CH:3]=1.CC[N:23]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=2)[C:9]([NH2:23])=[O:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 54205250HCID 54205250, compound

Product 1

HCID 68494892HCID 68494892, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

To a mixture 2-(4-fluorophenyl)-3-(4-methylthiophenyl)acrylic acid (prepared according to procedure given in Example 1) (3 g, 10.4 mmol), EDCI (4 g, 20.8 mmol), HOBt (1.4 g, 10.4 mmol) in DMF (35 mL) and triethylamine (3 mL, 20.8 mmol) was added slowly and stirred for 30 min. Reaction mixture was cooled to 5° C. and anhydrous ammonia gas purged for 10 min and stirred at 30° C. for 30 min. Reaction mixture was poured into water (250 mL) and extracted with ethyl acetate (2×200 mL). Combined organic layer was successively washed with water (3×200 mL) and brine solution (1×150 mL), dried over anhydrous sodium sulfate (2 g) and concentrated to afford the crude compound. The crude compound was triturated with hexane:ethyl acetate (9:1) (40 mL) for 3 times to afford a title compound as colorless solid (2 g, 67% yield).

Workup

  1. customReaction mixture
  2. customanhydrous ammonia gas purged for 10 min
  3. stirringstirred at 30° C. for 30 min
  4. customReaction mixture
  5. extractionextracted with ethyl acetate (2×200 mL)
  6. washCombined organic layer was successively washed with water (3×200 mL) and brine solution (1×150 mL)
  7. dry with materialdried over anhydrous sodium sulfate (2 g)
  8. concentrationconcentrated
  9. customto afford the crude compound
  10. customThe crude compound was triturated with hexane:ethyl acetate (9:1) (40 mL) for 3 times

Sources & evidence

ORD record
ord-38518f1c144d4b20a82629cd10ce297b
Source dataset
uspto-grants-2013_07
Patent number
US08476255B2

Reaction notes

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