Triethylamine → HCID 178506388, compound

HRID 1963927Notes

Reaction equation

HRID 1963927 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[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:22][CH:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[N:16]=3)[C:12]([Cl:29])=[CH:11][N:10]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.FC(F)(F)S(O[CH2:43][CH2:44][O:45][C:46]([F:49])([F:48])[F:47])(=O)=O>C(Cl)(Cl)Cl>[Cl:29][C:12]1[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:22][CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[N:16]=2)=[CH:14][C:9]([NH:8][C@H:5]2[CH2:6][CH2:7][C@H:2]([NH:1][CH2:43][CH2:44][O:45][C:46]([F:49])([F:48])[F:47])[CH2:3][CH2:4]2)=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 106351812-(Trifluoromethoxy)ethyl trifluoromethanesulfonateHCID 178511591HCID 178511591, compound

Product 1

HCID 178506388HCID 178506388, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of N2′-(trans-4-aminocyclohexyl)-5′-chloro-N6-((tetrahydro-2H-pyran-4-yl)methyl)-2,4′-bipyridine-2′,6-diamine (42 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 32 mg of 5′-chloro-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): 528.4 (MH+), retention time=0.53 min.; 1H NMR (400 MHz, DMSO-d6) d ppm 1.09-1.34 (m, 4 H) 1.35-1.54 (m, 2 H) 1.55-1.69 (m, 2 H) 1.73-1.89 (m, 1 H) 1.94-2.17 (m, 4H) 3.04-3.15 (m, 1 H) 3.14-3.20 (m, 2 H) 3.20-3.30 (m, 2 H) 3.30-3.47 (m, 2 H) 3.55-3.72 (m, 1 H) 3.84 (dd, J=11.15, 2.54 Hz, 2 H) 4.35 (t, J=4.70 Hz, 2 H) 6.65 (s, 1 H) 6.67-6.83 (m, 2 H) 7.05 (br. s., 0 H) 7.46-7.68 (m, 0 H) 8.06 (s, 0 H) 8.82 (d, J=3.52 Hz, 2H)

Workup

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

Sources & evidence

ORD record
ord-c7517f19dc1b45a29b622d96ae3d0c36
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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