1-Methyl-3-aminopyrazole → HCID 25261181、化合物

HRID 1966232ノート

反応式

HRID 1966232 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][N:3]=1.[CH3:14][N:15]1[CH:19]=[CH:18][C:17]([NH2:20])=[N:16]1>O1CCOCC1.Cl[Pd-](P(C1CC2CC1CC2)C1CC2CC1CC2)[C-]1C=CC=C1N(C)C.[CH-]1C=CC=C1.[Fe+2]>[CH:9]1([O:8][C:5]2[CH:6]=[CH:7][C:2]([NH:20][C:17]3[CH:18]=[CH:19][N:15]([CH3:14])[N:16]=3)=[N:3][CH:4]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

参加物

5

反応物 2

HCID 1372541-Methyl-3-aminopyrazoleHCID 578216902-Bromo-5-(cyclopentyloxy)pyridine

生成物 1

HCID 25261181HCID 25261181、化合物収率 29%

試薬・触媒・溶媒 2

HCID 178482626HCID 178482626、化合物触媒HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
80 °C

実験手順

2-Bromo-5-cyclopentyloxy-pyridine (0.97 mmol), sodium-tert.-butylate (1.4 eq.), and 1-methyl-1H-pyrazole-3-amine (1.2 eq.) are dissolved in degassed dioxane (2 ml) and heated to 80° C. Chloro-(di-2-norbornylphosphino)(2-dimethylaminoferrocene-1-yl)palladium (II) (3 mg) in degassed dioxane (1 ml) is added and the reaction mixture is heated for 1 hour at 150° C. in the microwave. The reaction is quenched with ethylacetate/methanol (30 ml, 9:1) and filtrated over celite. The solvent of the filtrate is removed in vacuo. (5-Cyclopentyloxy-pyridine-2-yl)-(1-methyl-1H-pyrazole-3-yl)-amine (“A25”) is obtained after reversed phase column chromatography (water/acetonitrile+0.1% TEA) as a colorless powder in a yield of 29%; HPLC (method C): 1.55 min; LC-MS (method A): 0.97 min, 259.15 (M+H+);

後処理

  1. temperaturethe reaction mixture is heated for 1 hour at 150° C. in the microwave
  2. customThe reaction is quenched with ethylacetate/methanol (30 ml, 9:1)
  3. filtrationfiltrated over celite
  4. customThe solvent of the filtrate is removed in vacuo

出典と根拠

ORDレコード
ord-d4f8b1c7e6424e87ae4d5eabe87c8c93
出典データセット
uspto-grants-2013_04
特許番号
US08420642B2

反応ノート

読み込み中…