Trifluoroacetic acid → 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-bromopyridine-2-carbonitrile TFA salt

HRID 1504877Notes

Reaction equation

HRID 1504877 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]2[NH:17]C(=O)OC(C)(C)C)[CH:5]=[N:6][C:7]=1[C:8]#[N:9].[C:25]([OH:31])([C:27]([F:30])([F:29])[F:28])=[O:26]>ClCCl>[OH:31][C:25]([C:27]([F:30])([F:29])[F:28])=[O:26].[NH2:17][C@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]1[NH:10][C:4]1[CH:3]=[C:2]([Br:1])[C:7]([C:8]#[N:9])=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86716545tert-butyl (1S,2R)-2-(5-bromo-6-cyanopyridin-3-ylamino)cyclohexylcarbamate

Product 1

HCID 867317475-{[(1R,2S)-2-aminocyclohexyl]amino}-3-bromopyridine-2-carbonitrile TFA salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl {(1S,2R)-2-[(5-bromo-6-cyanopyridin-3-yl)amino]cyclohexyl}carbamate (PrepEx 1.1) (100 mg, 0.253 mmol) was suspended in dichloromethane (1 mL). TFA (0.390 mL, 5.06 mmol) was added, and the reaction mixture was maintained at room temperature for 1.5 hours. The reaction mixture was concentrated under reduced pressure to afford 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-bromopyridine-2-carbonitrile TFA salt. The material was used without further purification in the subsequent transformation. MS ESI calc'd. for C12H16BrN4 [M+H]+ 295 and 297. found 295 and 297.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cd8d92b055054fc1b53d4d869db66cff
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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