Trifluoroacetic acid → 3-(6-Methyl-4-(3-methylisoxazol-4-yl)pyridin-2-ylamino)picolinonitrile

HRID 1504876Notes

Reaction equation

HRID 1504876 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6](N[C@@H]2CCCC[C@@H]2NC(=O)OC(C)(C)C)=[CH:5][C:4]=1[NH:24][C:25]1[CH:30]=[C:29]([C:31]2[C:32]([CH3:36])=[N:33][O:34][CH:35]=2)[CH:28]=[C:27]([CH3:37])[N:26]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:37][C:27]1[N:26]=[C:25]([NH:24][C:4]2[C:3]([C:1]#[N:2])=[N:8][CH:7]=[CH:6][CH:5]=2)[CH:30]=[C:29]([C:31]2[C:32]([CH3:36])=[N:33][O:34][CH:35]=2)[CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86731745tert-butyl (1S,2R)-2-(6-cyano-5-(6-methyl-4-(3-methylisoxazol-4-yl)pyridin-2-ylamino)pyridin-3-ylamino)cyclohexylcarbamate

Product 1

HCID 867317463-(6-Methyl-4-(3-methylisoxazol-4-yl)pyridin-2-ylamino)picolinonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl (1S,2R)-2-(6-cyano-5-(6-methyl-4-(3-methylisoxazol-4-yl)pyridin-2-ylamino)pyridin-3-ylamino)cyclohexylcarbamate (50 mg, 0.099 mmol) in DCM (1 ml) was added TFA (1.0 ml, 13 mmol). The reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was concentrated under reduced pressure to give 54(1R,2S)-2-aminocyclohexylamino)-3-(6-methyl-4-(3-methylisoxazol-4-yl)pyridin-2-ylamino)picolinonitrile. MS ESI calc'd. for C22H26N7O [M+H]+ 404. found 404.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6a0b286cdced4dbfaa43f23fa11fee50
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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