Trifluoroacetic acid → 5-((1R,2S)-2-aminocyclohexylamino)-3-(5-methyl-7,8-dihydroquinolin-2-ylamino)picolinonitrile

HRID 1504890노트

반응식

HRID 1504890 반응식
[C:1]([C:3]1[N:8]=[CH:7][C:6]([NH:9][C@@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]2[NH:16]C(=O)OC(C)(C)C)=[CH:5][C:4]=1[NH:24][C:25]1[CH:34]=[CH:33][C:32]2[C:31](O)([CH3:35])[CH2:30][CH2:29][CH2:28][C:27]=2[N:26]=1)#[N:2].FC(F)(F)C(O)=O>ClCCl.C1(C)C=CC=CC=1>[NH2:16][C@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][C@H:10]1[NH:9][C:6]1[CH:5]=[C:4]([NH:24][C:25]2[CH:34]=[CH:33][C:32]3[C:31]([CH3:35])=[CH:30][CH2:29][CH2:28][C:27]=3[N:26]=2)[C:3]([C:1]#[N:2])=[N:8][CH:7]=1

참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acidHCID 86731763tert-butyl (1S,2R)-2-(6-cyano-5-(5-hydroxy-5-methyl-5,6,7,8-tetrahydroquinolin-2-ylamino)pyridin-3-ylamino)cyclohexylcarbamate

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매2회

실험 절차

To a suspension of tert-butyl (1S,2R)-2-(6-cyano-5-(5-hydroxy-5-methyl-5,6,7,8-tetrahydroquinolin-2-ylamino)pyridin-3-ylamino)cyclohexylcarbamate (25 mg, 0.051 mmol) in dichlormethane (1.5 mL) was added trifluoroacetic acid (0.5 mL). After 20 minutes, the reaction mixture was diluted with toluene (1 mL) and dichloromethane (10 mL), and then concentrated under reduced pressure. The residue was dissolved in methanol (1 mL) and toluene (1 mL) and then concentrated under reduced pressure. This entire procedure was repeated again to afford 5-((1R,2S)-2-aminocyclohexylamino)-3-(5-methyl-7,8-dihydroquinolin-2-ylamino)picolinonitrile which was used without further purification. MS ESI calc'd. for C22H27N6 [M+H]+ 375. found 375.

후처리

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (1 mL)
  3. concentrationtoluene (1 mL) and then concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-fdb2d0ee62b247389453a81a8ed0aa5c
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216173B2

반응 노트

불러오는 중…