Triethylamine → HCID 178506389, compound

HRID 1963928Notes

Reaction equation

HRID 1963928 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:14]=[C:13]([C:15]3[C:20]([Cl:21])=[CH:19][CH:18]=[C:17]([NH:22][CH2:23][CH:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[N:16]=3)[C:12]([Cl:30])=[CH:11][N:10]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.FC(F)(F)S(O[CH2:44][CH2:45][O:46][C:47]([F:50])([F:49])[F:48])(=O)=O>C(Cl)(Cl)Cl>[Cl:21][C:20]1[C:15]([C:13]2[C:12]([Cl:30])=[CH:11][N:10]=[C:9]([NH:8][C@H:5]3[CH2:6][CH2:7][C@H:2]([NH:1][CH2:44][CH2:45][O:46][C:47]([F:50])([F:49])[F:48])[CH2:3][CH2:4]3)[CH:14]=2)=[N:16][C:17]([NH:22][CH2:23][CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 106351812-(Trifluoromethoxy)ethyl trifluoromethanesulfonateHCID 178511605HCID 178511605, compound

Product 1

HCID 178506389HCID 178506389, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of N2′-(trans-4-aminocyclohexyl)-3,5′-dichloro-N6-((tetrahydro-2H-pyran-4-yl)methyl)-2,4′-bipyridine-2′,6-diamine (45 mg, 0.10 mmol) and triethylamine (0.028 mL, 0.20 mmol) in chloroform (0.4 ml) was added 2-(trifluoromethoxy)ethyl trifluoromethanesulfonate (39 mg, 0.15 mmol). The mixture was stirred at ambient temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, purified by reverse phase HPLC, and lyophilized to give 29 mg of 3,5′-dichloro-N6-((tetrahydro-2H-pyran-4-yl)methyl)-N2′-(trans-4-(2-(trifluoromethoxy)ethylamino)cyclohexyl)-2,4′-bipyridine-2′,6-diamine as its TFA salt. LCMS (m/z): 562.4 (MH+), retention time=0.67 min.; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.07-1.32 (m, 4 H) 1.36-1.52 (m, 2 H) 1.58 (d, J=12.91 Hz, 2 H) 1.65-1.84 (m, 1 H) 2.07 (d, J=10.56 Hz, 4 H) 2.99-3.17 (m, 3 H) 3.23 (t, J=10.76 Hz, 2 H) 3.35 (br. s., 2 H) 3.64 (br. s., 1 H) 3.72-3.89 (m, 2 H) 4.34 (t, J=4.89 Hz, 2 H) 6.32-6.47 (m, 1 H) 6.49-6.65 (m, 1 H) 6.67-7.10 (m, 2 H) 7.49 (d, J=9.00 Hz, 1 H) 8.03 (s, 1 H) 8.75 (d, J=3.91 Hz, 1 H)

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-ceae6c985e65420b84b521f81f7e7c8c
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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