NSC636635 → HCID 21110168, compound

HRID 1766365Notes

Reaction equation

HRID 1766365 reaction equation
CC1(C)OC(=O)[C:5](=[CH:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[C:4](=O)[O:3]1.[F:20][C:21]([F:38])([F:37])[C:22]1[CH:23]=[C:24]([NH:28]/[C:29](/[CH3:36])=[CH:30]/[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:25]=[CH:26][CH:27]=1>COCCOCCOC.O>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([CH:9]2[CH2:5][C:4](=[O:3])[N:28]([C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([C:21]([F:37])([F:38])[F:20])[CH:23]=3)[C:29]([CH3:36])=[C:30]2[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:11][CH:12]=1)#[N:15]

Participants

5

Reactant 2

HCID 367166NSC636635HCID 11550816HCID 11550816, compound

Product 1

HCID 21110168HCID 21110168, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8150DiglymeSolvent

Procedure

4-[(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]benzonitrile (Example 18A; 200 mg, 0.77 mmol) and ethyl (2E)-3-{[3-(trifluoromethyl)phenyl]amino}-2-butenoate (212.4 mg, 0.77 mmol) are dissolved in 1-methoxy-2-(2-methoxyethoxy)ethane (3 ml). The solution is stirred at reflux temperature overnight. The reaction mixture is cooled to room temperature and diluted with water (5 ml). After extraction with toluene (2×5 ml), it is dried with anhydrous sodium sulphate, filtered, and the solvent is removed in vacuo. The product is purified via preparative HPLC.

Workup

  1. temperatureat reflux temperature overnight
  2. extractionAfter extraction with toluene (2×5 ml), it
  3. dry with materialis dried with anhydrous sodium sulphate
  4. filtrationfiltered
  5. customthe solvent is removed in vacuo
  6. customThe product is purified via preparative HPLC

Sources & evidence

ORD record
ord-2f950937b7e44c45a351f5af1fef1b66
Source dataset
uspto-grants-2007_06
Patent number
US07230017B2

Reaction notes

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