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

HRID 1504891노트

반응식

HRID 1504891 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-80f620d30ebf4a56b8aff0e35bb8b0ed
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216173B2

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