Trifluoroacetic acid → 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(5-cyano-6-methylpyridin-2-yl)amino]pyridine-2-carbonitrile

HRID 1504869Notes

Reaction equation

HRID 1504869 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:30]=[CH:29][C:28]([C:31]#[N:32])=[C:27]([CH3:33])[N:26]=1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[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:30]=[CH:29][C:28]([C:31]#[N:32])=[C:27]([CH3:33])[N:26]=2)[C:3]([C:1]#[N:2])=[N:8][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86731737HCID 86731737, compound

Product 1

HCID 867317385-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(5-cyano-6-methylpyridin-2-yl)amino]pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [(1S,2R)-2-({6-cyano-5-[(5-cyano-6-methylpyridin-2-yl)amino]pyridin-3-yl}amino)cyclohexyl]carbamate (58 mg, 0.13 mmol) in dichloromethane (1.3 mL) was added trifluoroacetic acid (1.0 mL, 13 mmol) at room temperature. After 16 hours, the reaction mixture was concentrated under reduced pressure to afford 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(5-cyano-6-methylpyridin-2-yl)amino]pyridine-2-carbonitrile. The material was used in the next step without further purification. MS ESI calc'd for C19H22N7 [M+H]+ 348. found 348.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a74423e36fb04271b1a3b3cae98c0def
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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