Water → 5-((1R,2R)-2-amino-3,3-difluorocyclohexylamino)-3-chloropyrazine-2-carbonitrile

HRID 2200426Notes

Reaction equation

HRID 2200426 reaction equation
[Cl:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6](Cl)[N:7]=1.Cl.Cl.[F:13][C:14]1([F:22])[CH2:19][CH2:18][CH2:17][C@@H:16]([NH2:20])[C@H:15]1[NH2:21].CCN(C(C)C)C(C)C.O>CN(C=O)C.CCOC(C)=O>[NH2:21][C@H:15]1[C:14]([F:22])([F:13])[CH2:19][CH2:18][CH2:17][C@H:16]1[NH:20][C:6]1[N:7]=[C:2]([Cl:1])[C:3]([C:9]#[N:10])=[N:4][CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 529877443,5-Dichloropyrazine-2-carbonitrileHCID 86685557(1R,2R)-3,3-difluorocyclohexane-1,2-diamine dihydrochloride

Product 1

HCID 866855565-((1R,2R)-2-amino-3,3-difluorocyclohexylamino)-3-chloropyrazine-2-carbonitrileYield 90.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3,5-dichloropyrazine-2-carbonitrile (102 mg, 0.586 mmol), (1R,2R)-3,3-difluorocyclohexane-1,2-diamine dihydrochloride (132 mg, 0.591 mmol) and DIEA (0.400 mL, 2.30 mmol) in DMF (2 mL) was stirred at room temperature for 20 h. Water and EtOAc were added. Organic phase was separated, washed with water, dried over Na2SO4, concentrated in vacuo to give 5-((1R,2R)-2-amino-3,3-difluorocyclohexylamino)-3-chloropyrazine-2-carbonitrile (153 mg).

Workup

  1. customOrganic phase was separated
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee6c72c706734c4e832312e59f222928
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

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