Potassium trimethylsilanolate → 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(5-methyl-7,8-dihydroquinolin-2-yl)amino]pyridine-2-carboxamide

HRID 1504891ノート

反応式

HRID 1504891 の反応式
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[CH:10]=[C:11]([NH:17][C:18]2[CH:27]=[CH:26][C:25]3[C:24]([CH3:28])=[CH:23][CH2:22][CH2:21][C:20]=3[N:19]=2)[C:12]([C:15]#[N:16])=[N:13][CH:14]=1.C[Si](C)(C)[O-:31].[K+]>O1CCOCC1>[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[CH:10]=[C:11]([NH:17][C:18]2[CH:27]=[CH:26][C:25]3[C:24]([CH3:28])=[CH:23][CH2:22][CH2:21][C:20]=3[N:19]=2)[C:12]([C:15]([NH2:16])=[O:31])=[N:13][CH:14]=1

参加物

4

反応物 2

HCID 23668039Potassium trimethylsilanolateHCID 867317645-((1R,2S)-2-aminocyclohexylamino)-3-(5-methyl-7,8-dihydroquinolin-2-ylamino)picolinonitrile

生成物 1

HCID 867317655-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(5-methyl-7,8-dihydroquinolin-2-yl)amino]pyridine-2-carboxamide

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A suspension of 5-((1R,2S)-2-aminocyclohexylamino)-3-(5-methyl-7,8-dihydroquinolin-2-ylamino)picolinonitrile (19 mg, 0.051 mmol) and potassium trimethylsilanolate (98 mg, 0.76 mmol) in 1,4-dioxane (1 mL) was heated to 100° C. in an oil bath for 3 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was diluted with DMSO, filtered, and purified by reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient) to yield 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(5-methyl-7,8-dihydroquinolin-2-yl)amino]pyridine-2-carboxamide. MS ESI calc'd. for C22H29N6O [M+H]+ 393. found 393.

後処理

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with DMSO
  4. filtrationfiltered
  5. custompurified by reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient)

出典と根拠

ORDレコード
ord-80f620d30ebf4a56b8aff0e35bb8b0ed
出典データセット
uspto-grants-2015_12
特許番号
US09216173B2

反応ノート

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