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

HRID 1504890Notes

Reaction equation

HRID 1504890 reaction equation
[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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-fdb2d0ee62b247389453a81a8ed0aa5c
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

Loading…