Trifluoroacetic acid → 5-{[(2S)-2-aminopropyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile TFA salt

HRID 1504859Notes

Reaction equation

HRID 1504859 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([NH:9][CH2:10][C@@H:11]([NH:13]C(=O)OC(C)(C)C)[CH3:12])=[CH:5][C:4]=1[NH:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[N:23]=1)#[N:2].[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33]>C(Cl)Cl>[OH:34][C:32]([C:31]([F:36])([F:35])[F:30])=[O:33].[NH2:13][C@@H:11]([CH3:12])[CH2:10][NH:9][C:6]1[CH:5]=[C:4]([NH:21][C:22]2[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[N:23]=2)[C:3]([C:1]#[N:2])=[N:8][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86731724tert-butyl [(2S)-1-({6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}amino)propan-2-yl]carbamate

Product 1

HCID 867317255-{[(2S)-2-aminopropyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile TFA salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask containing tert-butyl [(2S)-1-({6-cyano-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl}amino)propan-2-yl]carbamate (160 mg, 0.404 mmol) were added DCM (3 mL) and trifluoroacetic acid (0.3 mL). After 1 hour, the reaction mixture was concentrated under reduced pressure to afford 5-{[(2S)-2-aminopropyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile TFA salt. The material was used without further purification. MS ESI calc'd. for C16H21N6 [M+H]+ 297. found 297.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-171d0ea24b86482cba6a0508c775f8b8
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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