Water → HCID 178511129, compound

HRID 1506182Notes

Reaction equation

HRID 1506182 reaction equation
[C:1]1([C@H:13]2[CH2:18][CH2:17][C@H:16]([CH:19]=[C:20]([C:23]#[N:24])[C:21]#[N:22])[CH2:15][CH2:14]2)[N:2]=[N:3][N:4]2[C:9]=1[C:8]1[CH:10]=[CH:11][NH:12][C:7]=1[N:6]=[CH:5]2.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O.O>O1CCCC1>[C:1]1([C@H:13]2[CH2:14][CH2:15][C@H:16]([CH2:19][CH:20]([C:23]#[N:24])[C:21]#[N:22])[CH2:17][CH2:18]2)[N:2]=[N:3][N:4]2[C:9]=1[C:8]1[CH:10]=[CH:11][NH:12][C:7]=1[N:6]=[CH:5]2

Participants

5

Reactant 3

HCID 962WaterHCID 70849Hantzsch esterHCID 178511128HCID 178511128, compound

Product 1

HCID 178511129HCID 178511129, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-{[trans-4-(7H-Pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidin-1-yl)cyclohexyl]methylene}malononitrile (25.8 mg, 0.0812 mmol) in tetrahydrofuran (3 mL) was mixed with diethyl 1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate (30.8 mg, 0.122 mmol) and stirred at room temperature for 1 hours. After addition of water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1→1/2→0/1 (v/v)) to give the title compound as a colorless solid (14.2 mg, yield 55%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous ammonium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1→1/2→0/1 (v/v))

Sources & evidence

ORD record
ord-ac023269da8e4530ae77e2f9d1e9f0cf
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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