HCID 66937096, compound → HCID 178511608, compound

HRID 1963917Notes

Reaction equation

HRID 1963917 reaction equation
[Cl:1][C:2]1[C:3]([C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:12]=[N:11][C:10]=2[C:23]([F:26])([F:25])[F:24])=[CH:4][C:5](F)=[N:6][CH:7]=1.[C@H:27]1([NH2:34])[CH2:32][CH2:31][C@H:30]([NH2:33])[CH2:29][CH2:28]1>CS(C)=O>[Cl:1][C:2]1[C:3]([C:9]2[C:10]([C:23]([F:26])([F:25])[F:24])=[N:11][CH:12]=[C:13]([NH:15][CH2:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[N:14]=2)=[CH:4][C:5]([NH:33][C@H:30]2[CH2:31][CH2:32][C@H:27]([NH2:34])[CH2:28][CH2:29]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 66937096HCID 66937096, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178511608HCID 178511608, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

6-(5-chloro-2-fluoropyridin-4-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)-5-(trifluoromethyl)pyrazin-2-amine (0.0178 g, 0.046 mmol) was dissolved in anhydrous DMSO (1.0 ml) and charged to a microwave vial. This was treated with trans-cyclohexane-1,4-diamine (0.052 g, 0.456 mmol). The reaction mixture was then heated at 100° C. for 18 hr. The reaction mixture was allowed to cool to ambient temperature. The material was purified by preparative reverse-phase HPLC to give 0.0086 g (32%) of trans-N1-(5-chloro-4-(6-((tetrahydro-2H-pyran-4-yl)methyl)amino-3-(trifluoromethyl)pyrazin-2-yl)pyridin-2-yl)cyclohexane-1,4-diamine as the TFA salt. LCMS (m/z): 485.3 (MH+), retention time=0.63 min.

Workup

  1. additioncharged to a microwave vial
  2. temperatureto cool to ambient temperature
  3. customThe material was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-6febcc1dda3c43b99c6d24086cab8aa0
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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