Diisopropylethylamine → HCID 178430628, compound

HRID 1623402Notes

Reaction equation

HRID 1623402 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[N:9]=2)[C:5]([CH3:23])=[CH:4][N:3]=1.[C@H:24]1([NH2:31])[CH2:29][CH2:28][C@H:27]([NH2:30])[CH2:26][CH2:25]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.O>[NH2:30][C@H:27]1[CH2:28][CH2:29][C@H:24]([NH:31][C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=4)[N:9]=3)[C:5]([CH3:23])=[CH:4][N:3]=2)[CH2:25][CH2:26]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 66936939HCID 66936939, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178430628HCID 178430628, compoundYield 17.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 2′-fluoro-N-(3-fluorobenzyl)-5′-methyl-2,4′-bipyridin-6-amine (18 mg, 0.058 mmol) and trans-cyclohexane-1,4-diamine (39.6 mg, 0.347 mmol), in NMP (0.3 mL) was added DIPEA (20 μL, 0.115 mmol). The mixture was heated at 130° C. for 48 h. The mixture was allowed to cool then diluted with water and then extracted with EtOAc (×3). The combined organics were washed with saturated brine (×2), then dried (Na2SO4), filtered and evaporated under reduced pressure. The resulting residue was purified by reverse phase preparative HPLC and then lyophallized to yield N2′-(trans-4-aminocyclohexyl)-N6-(3-fluorobenzyl)-5′-methyl-2,4′-bipyridine-2′,6-diamine (4.2 mg), LCMS (m/z): 406.3 (MH+), retention time=0.53 min as a TFA salt.

Workup

  1. temperatureto cool
  2. extractionextracted with EtOAc (×3)
  3. washThe combined organics were washed with saturated brine (×2)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe resulting residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-645d306190a84150b7fd42bc9d633103
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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