Dichloromethane → HCID 118023268, compound

HRID 2171821Notes

Reaction equation

HRID 2171821 reaction equation
[CH:1]1([C:7]2[S:24][C:10]3[N:11]=[C:12]([CH3:23])[N:13]=[C:14]([CH2:15][NH:16][CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)[C:9]=3[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)Cl.[C:28](Cl)(=[O:30])[CH3:29]>O>[CH:17]1([N:16]([CH2:15][C:14]2[C:9]3[CH:8]=[C:7]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)[S:24][C:10]=3[N:11]=[C:12]([CH3:23])[N:13]=2)[C:28](=[O:30])[CH3:29])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 118023161HCID 118023161, compound

Product 1

HCID 118023268HCID 118023268, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of N-[(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methyl]cyclohexaneamine (47 mg) and DCM (4 mL) were added dropwise acetyl chloride (20 μL) and TEA (40 μL) at 0° C., followed by stirring at room temperature for 2.5 hours. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was washed sequentially with 1 M hydrochloric acid, saturated aqueous sodium bicarbonate, and brine, dried over MgSO4, and then concentrated under reduced pressure to obtain N-cyclohexyl-N-[(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methyl]acetamide (50 mg).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed sequentially with 1 M hydrochloric acid, saturated aqueous sodium bicarbonate, and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f54051ad51ef4e02b3365398b465ee49
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

Loading…