3-Fluorobenzylamine → HCID 11579573, compound

HRID 1623289Notes

Reaction equation

HRID 1623289 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[F:9][C:10]1[CH:11]=[C:12]([CH2:16][NH2:17])[CH:13]=[CH:14][CH:15]=1>CS(C)=O>[Cl:8][C:4]1[N:3]=[C:2]([NH:17][CH2:16][C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([F:9])[CH:11]=2)[CH:7]=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 668533-FluorobenzylamineHCID 785042,6-Dichloropyrazine

Product 1

HCID 11579573HCID 11579573, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
90 °C

Procedure

To 2,6-dichloropyrazine (175 mg, 1.175 mmol) was added DMSO (1.5 ml), TEA (0.196 ml, 1.410 mmol) and (3-fluorophenyl)methanamine (368 mg, 2.94 mmol) l. The reaction mixture then was stirred at 90° C. until completion as indicated by LCMS, about 1 hour. To the reaction mixture was added 3 ml of DMSO, filtered and the residue was purified by prep LC. After lyphilization, 160 mg of the title compound was obtained as a TFA. LCMS (m/z): 238.1 (MH+), retention time=0.96 min.

Workup

  1. customas indicated by LCMS, about 1 hour
  2. filtrationfiltered
  3. customthe residue was purified by prep LC

Sources & evidence

ORD record
ord-7af75d19f2fb4ed2b5ff9ab666704585
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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