Triethylamine → (7-Chlorothieno[3,2-b]pyridin-2-yl)(4-methylpiperazin-1-yl)methanone

HRID 1400944Notes

Reaction equation

HRID 1400944 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Cl:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18](Cl)=[O:19])[S:17][C:10]=12.CCN(CC)CC>C(Cl)Cl.O>[Cl:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[O:19])[S:17][C:10]=12

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 221435437-Chlorothieno[3,2-b]pyridine-2-carbonyl chloride

Product 1

HCID 58474741(7-Chlorothieno[3,2-b]pyridin-2-yl)(4-methylpiperazin-1-yl)methanoneYield 91.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-Methylpiperazine (0.574 mL, 5.17 mmol) was added to a suspension of 7-chlorothieno[3,2-b]pyridine-2-carbonyl chloride (435, 1 g, 4.31 mmol) and Et3N (1.80 mL, 12.93 mmol) in DCM (50 mL). The reaction mixture was stirred for 1 h at room temperature, diluted with water and a saturated aqueous solution of ammonium chloride and extracted with DCM. The organic layer was successively washed with a saturated aqueous solution of ammonium chloride and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by biotage (SNAP 25 g cartridge; MeOH/DCM: 0/100 to 10/90 over 20CV), to afford the title compound 436 (1.16 g, 3.93 mmol, 91% yield) as a yellow solid. MS (m/z): 296.2 (M+H).

Workup

  1. extractiona saturated aqueous solution of ammonium chloride and extracted with DCM
  2. washThe organic layer was successively washed with a saturated aqueous solution of ammonium chloride and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by biotage (SNAP 25 g cartridge; MeOH/DCM: 0/100 to 10/90 over 20CV)

Sources & evidence

ORD record
ord-c5c8457b7699425abb27e76defb3ada6
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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