(5-Nitro-4-thiocyanato-pyrimidin-2-yl)-phenethyl-amine → HCID 178511550, compound

HRID 1819408Notes

Reaction equation

HRID 1819408 reaction equation
[N+:1]([C:4]1[C:5](SC#N)=[N:6][C:7]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:8][CH:9]=1)([O-:3])=[O:2].[NH2:22][CH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([NH:30]C(=O)OC(C)(C)C)[CH2:26][CH2:25]1>C(Cl)Cl>[NH2:30][C@H:27]1[CH2:28][CH2:29][C@H:24]([CH2:23][NH:22][C:5]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=[C:7]([NH:10][CH2:11][CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:6]=2)[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 57885571(5-Nitro-4-thiocyanato-pyrimidin-2-yl)-phenethyl-amineHCID 178453944HCID 178453944, compound

Product 1

HCID 178511550HCID 178511550, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the above (5-nitro-4-thiocyanato-pyrimidin-2-yl)-phenethyl-amine (75 mg, 0.25 mmol) in CH2Cl2 was added tert-butyl trans-4-aminomethylcyclohexylcarbamate (114 mg, 0.5 mmol). The reaction mixture was stirred at room temperature for 16 h and concentrated in vacuo. The resulting residue was then diluted with CH2Cl2 (1 mL) and TFA (0.5 mL) was added. The mixture was stirred at room temperature for 4 h and concentrated in vacuo. The resulting residue was purified by preparative LCMS to afford 36 mg (39%) of the title compound, m/z 371.6 [M+1]+.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe resulting residue was then diluted with CH2Cl2 (1 mL) and TFA (0.5 mL)
  3. additionwas added
  4. stirringThe mixture was stirred at room temperature for 4 h
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by preparative LCMS

Sources & evidence

ORD record
ord-7fa12f6f6e0c4ef390721f0b9dce0be3
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

Loading…