Triethylamine → (R)-(-)-N-(1,1,3-trimethylindan-4-yl)-1,3,5-trimethylpyrazole-4-carboxamide

HRID 2040396

Reaction equation

HRID 2040396 reaction equation
[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[C:6]([NH2:11])[CH:7]=[CH:8][CH:9]=2)[C@H:4]([CH3:12])[CH2:3]1.C(N(CC)CC)C.[CH3:21][N:22]1[C:26]([CH3:27])=[C:25]([C:28](Cl)=[O:29])[C:24]([CH3:31])=[N:23]1>CN(C)C1C=CN=CC=1.C1COCC1>[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[C:6]([NH:11][C:28]([C:25]3[C:24]([CH3:31])=[N:23][N:22]([CH3:21])[C:26]=3[CH3:27])=[O:29])[CH:7]=[CH:8][CH:9]=2)[C@H:4]([CH3:12])[CH2:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13637622trimethyl-1H-pyrazole-4-carbonyl chlorideHCID 14535936(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-amine

Product 1

HCID 54756490(R)-(-)-N-(1,1,3-trimethylindan-4-yl)-1,3,5-trimethylpyrazole-4-carboxamideYield 63.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Into a solution composed of 0.15 g of (R)-1,1,3-trimethyl-4-aminoindane (optical purity: 99% ee), 0.13 g of triethylamine, 5 mg of 4-dimethylaminopyridine and 1 mL of THF, a solution of 0.15 g of 1,3,5-trimethylpyrazole-4-carbonyl chloride in THF was dropped under ice cool. The mixture was stirred at room temperature for 15 minutes, then, to the reaction mixture was added ice water, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and saturated saline sequentially, then, dried over magnesium sulfate and concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.17 g of (R)-(−)-N-(1,1,3-trimethylindan-4-yl)-1,3,5-trimethylpyrazole-4-carboxamide (hereinafter, referred to as present carboxamide compound (3)) (optical purity: 99% ee).

Workup

  1. temperaturecool
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution and saturated saline sequentially
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2473535aa63a42ae94d5341995a2d87d
Source dataset
uspto-grants-2013_11
Patent number
US08580836B2

Linked notes

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