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

HRID 2040396

反応式

HRID 2040396 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2473535aa63a42ae94d5341995a2d87d
出典データセット
uspto-grants-2013_11
特許番号
US08580836B2

関連ノート

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