tert-butyl (1S,2R)-2-(5-cyano-6-(1-methyl-1H-indol-4-ylamino)pyrazin-2-ylamino)cyclohexylcarbamate → 5-((1R,2S)-2-aminocyclohexylamino)-3-(1-methyl-1H-indol-4-ylamino)pyrazine-2-carbonitrile

HRID 332743Notes

Reaction equation

HRID 332743 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:20][C@@H:21]2[CH2:26][CH2:25][CH2:24][CH2:23][C@@H:22]2[NH:27]C(=O)OC(C)(C)C)=[N:7][C:8]=1[NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[CH:13][N:14]2[CH3:19])#[N:2]>C(O)(C(F)(F)F)=O>[NH2:27][C@H:22]1[CH2:23][CH2:24][CH2:25][CH2:26][C@H:21]1[NH:20][C:6]1[N:7]=[C:8]([NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[CH:12]=[CH:13][N:14]3[CH3:19])[C:3]([C:1]#[N:2])=[N:4][CH:5]=1

Participants

3

Reactant 1

HCID 86685548tert-butyl (1S,2R)-2-(5-cyano-6-(1-methyl-1H-indol-4-ylamino)pyrazin-2-ylamino)cyclohexylcarbamate

Product 1

HCID 866855495-((1R,2S)-2-aminocyclohexylamino)-3-(1-methyl-1H-indol-4-ylamino)pyrazine-2-carbonitrileYield 15%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The crude tert-butyl (1S,2R)-2-(5-cyano-6-(1-methyl-1H-indol-4-ylamino)pyrazin-2-ylamino)cyclohexylcarbamate (153 mg) was dissolved in TFA (4 mL). After being stirred at room temperature for 2 h, the mixture was concentrated in vacuo. The residue was purified by HPLC to give 5-((1R,2S)-2-aminocyclohexylamino)-3-(1-methyl-1H-indol-4-ylamino)pyrazine-2-carbonitrile (18 mg).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-ce954fa49f8e4e5698a5421fe6e219e1
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Reaction notes

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