HCID 66936831, compound → HCID 178511596, compound

HRID 1963871Notes

Reaction equation

HRID 1963871 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][NH:6][C:7]1[CH:12]=[N:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][N:16]=[C:15](F)[CH:14]=2)[N:8]=1.[C@H:23]1([NH2:30])[CH2:28][CH2:27][C@H:26]([NH2:29])[CH2:25][CH2:24]1>CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][NH:6][C:7]1[N:8]=[C:9]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:29][C@H:26]3[CH2:27][CH2:28][C@H:23]([NH2:30])[CH2:24][CH2:25]3)[CH:14]=2)[CH:10]=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 66936831HCID 66936831, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178511596HCID 178511596, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
105 °C

Procedure

To N-(3-fluorobenzyl)-6-(2-fluoropyridin-4-yl)pyrazin-2-amine (30 mg, 0.101 mmol) was added DMSO (0.6 ml) and trans-cyclohexane-1,4-diamine (115 mg, 1.006 mmol). The reaction mixture then was stirred at 105° C. until completion as indicated by LCMS, about 40 hours. To the crude reaction mixture, after cooling to room temperature mixture was added 0.75 ml of DMSO, the resulting mixture filtered and purified by prep LC. After lyophilization, 34 mg of the title compound was obtained as a TFA salt. LCMS (m/z): 393.2 (MH+), retention time=0.54 min.

Workup

  1. customas indicated by LCMS, about 40 hours
  2. customTo the crude reaction mixture
  3. temperatureafter cooling to room temperature mixture
  4. filtrationthe resulting mixture filtered
  5. custompurified by prep LC

Sources & evidence

ORD record
ord-e00355e3111049ff848ab088746565f2
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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