Water → 5'-chloro-N6-(3-fluorobenzyl)-N2'-methyl-2,4'-bipyridine-2',6-diamine

HRID 1963966Notes

Reaction equation

HRID 1963966 reaction equation
[Cl:1][C:2]1[C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)[N:10]=2)=[CH:4][C:5](F)=[N:6][CH:7]=1.[CH3:24][NH2:25].O>CS(C)=O>[Cl:1][C:2]1[C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)[N:10]=2)=[CH:4][C:5]([NH:25][CH3:24])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 58127193HCID 58127193, compound2×

Product 1

HCID 669370185'-chloro-N6-(3-fluorobenzyl)-N2'-methyl-2,4'-bipyridine-2',6-diamine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 5′-chloro-2′-fluoro-N-(3-fluorobenzyl)-2,4′-bipyridin-6-amine (Intermediate B) (15 mg, 0.045 mmol) was added DMSO (0.4 ml) and methyl amine 40% in water (200 μl, 2.293 mmol) in a microwave tube was micro waved at 145° C. for 900 seconds and the reaction progress was followed by LCMS. Most of the amine was removed under vacuum, 0.5 ml of DMSO was added, filtered and purified by prep LC. After lypholization 13.9 mg of the title compound was obtained as a TFA salt. LCMS (m/z): 343.0 (MH+), retention time=0.67 min.; 1H NMR (300 MHz, METHANOL-d4, 25° C.) δ ppm 2.97 (s, 3 H) 4.62 (s, 2 H) 6.81 (d, J=8.50 Hz, 1 H) 6.91-7.02 (m, 3 H) 7.09 (d, J=9.96 Hz, 1 H) 7.17 (d, J=7.62 Hz, 1 H) 7.27-7.39 (m, 1 H) 7.69 (dd, J=8.50, 7.33 Hz, 1 H) 8.03 (s, 1 H).

Workup

  1. customMost of the amine was removed under vacuum, 0.5 ml of DMSO
  2. additionwas added
  3. filtrationfiltered
  4. custompurified by prep LC

Sources & evidence

ORD record
ord-d11119aee5e142f39f3406289813da5e
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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