Triethylamine → HCID 178526821, compound

HRID 1819474Notes

Reaction equation

HRID 1819474 reaction equation
[N:1]1([CH:6]2[CH2:11][CH2:10][CH:9](NC)[CH2:8][CH2:7]2)[CH:5]=[CH:4][N:3]=[CH:2]1.C[CH2:15][N:16](CC)CC.[N+:21]([C:24]1[C:25](SC#N)=[N:26][C:27]([NH:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[O:38][C:39]([F:42])([F:41])[F:40])=[N:28][CH:29]=1)([O-:23])=[O:22]>CCO>[N:1]1([C@H:6]2[CH2:7][CH2:8][C@H:9]([CH2:15][NH:16][C:25]3[C:24]([N+:21]([O-:23])=[O:22])=[CH:29][N:28]=[C:27]([NH:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[O:38][C:39]([F:41])([F:42])[F:40])[N:26]=3)[CH2:10][CH2:11]2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 57885541(5-Nitro-4-thiocyanato-pyrimidin-2-yl)-(2-trifluoromethoxy-benzyl)-amineHCID 69055629(4-Imidazol-1-yl-cyclohexyl)-methylamine

Product 1

HCID 178526821HCID 178526821, compoundYield 32.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4-imidazol-1-yl-cyclohexyl)-methylamine (32 mg, 0.18 mmol) and Et3N (76 μL, 0.54 mmol) in EtOH (1 mL) was added (5-Nitro-4-thiocyanato-pyrimidin-2-yl)-(2-trifluoromethoxy-benzyl)-amine (71 mg, 0.19 mmol). The mixture was stirred at room temperature for 14 h before concentrating in vacuo. The residue was partially purified by column chromatography using a 12 g ISCO combi-flash cartridge (silica gel, 95:4.75:0.25 DCM/MeOH/NH4OH) then re-purified by semi-preparative HPLC. The isolated TFA salt was converted to the free base by partitioning between sat. NaHCO3 and EtOAc. Concentration of the organic layer in vacuo afforded 29 mg of the title compound as an off-white solid, m/z 492 [M+1]+

Workup

  1. concentrationbefore concentrating in vacuo
  2. customThe residue was partially purified by column chromatography
  3. customthen re-purified by semi-preparative HPLC
  4. customby partitioning between sat. NaHCO3 and EtOAc

Sources & evidence

ORD record
ord-bc8bd099ab694e48b3839875d475ed01
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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