Trifluoroacetic acid → rel-5-{[(3S,4S)-4-amino-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]amino}-3-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridine-2-carbonitrile

HRID 1504898Notes

Reaction equation

HRID 1504898 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([NH:9][C@H:10]2[C@@H:15]([NH:16]C(=O)OC(C)(C)C)[CH2:14][CH2:13][S:12](=[O:25])(=[O:24])[CH2:11]2)=[CH:5][C:4]=1[NH:26][C:27]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29]([CH3:35])[N:28]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:16][C@H:15]1[CH2:14][CH2:13][S:12](=[O:25])(=[O:24])[CH2:11][C@H:10]1[NH:9][C:6]1[CH:5]=[C:4]([NH:26][C:27]2[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29]([CH3:35])[N:28]=2)[C:3]([C:1]#[N:2])=[N:8][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90354236tert-butyl rel-[(3S,4S)-3-({6-cyano-5-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridin-3-yl}amino)-1,1-dioxidotetrahydro-2H-thiopyran-4-yl]carbamate

Product 1

HCID 90354286rel-5-{[(3S,4S)-4-amino-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]amino}-3-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl rel-[(3S,4S)-3-({6-cyano-5-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridin-3-yl}amino)-1,1-dioxidotetrahydro-2H-thiopyran-4-yl]carbamate (56 mg, 0.11 mmol) in DCM (2 mL) was added TFA (1 mL). After 30 minutes, the reaction mixture was concentrated under reduced pressure to afford rel-5-{[(3S,4S)-4-amino-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]amino}-3-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridine-2-carbonitrile, which was used directly in the next step without purification. MS ESI calc'd. for C18H23N6O3S [M+H]+ 403. found 403.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7cda88dad199421ca79c49492ac7ecae
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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