Cyclopentylamine → HCID 118023445, compound

HRID 2171802Notes

Reaction equation

HRID 2171802 reaction equation
CS(O[CH2:6][C:7]1[C:8]2[CH:16]=[C:15]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[S:14][C:9]=2[N:10]=[C:11]([CH3:13])[N:12]=1)(=O)=O.CC#N.[CH:26]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27]1>O>[CH:17]1([C:15]2[S:14][C:9]3[N:10]=[C:11]([CH3:13])[N:12]=[C:7]([CH2:6][NH:31][CH:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[C:8]=3[CH:16]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 6342AcetonitrileHCID 118023431HCID 118023431, compound

Product 1

HCID 118023445HCID 118023445, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of (6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methyl methanesulfonate (500 mg) and CH3CN (10 mL) was added cyclopentylamine (1.0 mL), followed by stirring at room temperature for 3 hours. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was dried over MgSO4 and then concentrated under reduced pressure. The residue was purified by basic silica gel column (hexane/EtOAc) and silica gel column (hexane/EtOAc) to obtain N-[(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methyl]cyclopentaneamine (326 mg).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column (hexane/EtOAc) and silica gel column (hexane/EtOAc)

Sources & evidence

ORD record
ord-679eacbef616498bb12d9d7795c202f5
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

Loading…