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

HRID 1504890Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1504890
[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

Komponenten

5

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-fdb2d0ee62b247389453a81a8ed0aa5c
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216173B2

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