3-Fluorobenzylamine → HCID 86650609, compound

HRID 1623293Notes

Reaction equation

HRID 1623293 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[N:3]=1.[F:13][C:14]1[CH:15]=[C:16]([CH2:20][NH2:21])[CH:17]=[CH:18][CH:19]=1>CS(C)=O>[Cl:12][C:4]1[N:3]=[C:2]([NH:21][CH2:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([F:13])[CH:15]=2)[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=1

Participants

4

Reactant 2

HCID 668533-FluorobenzylamineHCID 5209682,6-Dichloro-4-(trifluoromethyl)pyridine

Product 1

HCID 86650609HCID 86650609, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
90 °C

Procedure

To 2,6-dichloro-4-(trifluoromethyl)pyridine (250 mg, 1.157 mmol) was added DMSO (2 ml), TEA (0.194 ml, 1.389 mmol), and (3-fluorophenyl)methanamine (290 mg, 2.315 mmol). The reaction mixture was stirred at 90° C. until completion as indicated by LCMS, about 1 hour. To the crude reaction mixture was added 1.5 ml of DMSO, filtered and purified by prep LC. After lyphilization, 158 mg of the title compound was obtained as a TFA salt. LCMS (m/z): 305.1 (MH+), rt=1.21 min.

Workup

  1. customas indicated by LCMS, about 1 hour
  2. customTo the crude reaction mixture
  3. filtrationfiltered
  4. custompurified by prep LC

Sources & evidence

ORD record
ord-74e2b1ff9da14e11978989f849fc4476
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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