Cyclopentanemethylamine → HCID 118023423, compound

HRID 2171803Notes

Reaction equation

HRID 2171803 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.[CH:23]1(CN)[CH2:27][CH2:26][CH2:25][CH2:24]1.C[CH2:31][N:32](C(C)C)C(C)C.C(=O)(O)[O-].[Na+]>CC#N>[CH:17]1([C:15]2[S:14][C:9]3[N:10]=[C:11]([CH3:13])[N:12]=[C:7]([CH2:6][N:32]([CH3:31])[CH:23]4[CH2:24][CH2:25][CH2:26][CH2:27]4)[C:8]=3[CH:16]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 80153CyclopentanemethylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 118023431HCID 118023431, compound

Product 1

HCID 118023423HCID 118023423, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of (6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl methanesulfonate (150 mg), cyclopentylmethylamine (100 mg), and CH3CN (3 mL) was added DIPEA (200 μL), followed by stirring at room temperature overnight. To the reaction mixture was added saturated aqueous sodium bicarbonate, followed by extraction with EtOAc. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure, and the residue was purified by silica gel column (hexane/EtOAc) to obtain N-[(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methyl]-N-methylcyclopentaneamine (131 mg).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by silica gel column (hexane/EtOAc)

Sources & evidence

ORD record
ord-fec951a08b7d493398c3fdbe4e142f05
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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