Pyridine → HCID 66674274, compound

HRID 423423Notes

Reaction equation

HRID 423423 reaction equation
N1C=CC=CC=1.Cl.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:37][C:18]3[C:19](=[O:36])[N:20]([C:23]4[CH:24]=[N:25][C:26]([O:29][CH:30]5[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]5)=[CH:27][CH:28]=4)[CH:21]=[CH:22][C:17]=3[CH:16]=2)=[CH:11][CH:10]=1.[C:38](Cl)(=[O:40])[CH3:39]>ClCCl.O>[C:38]([N:33]1[CH2:34][CH2:35][CH:30]([O:29][C:26]2[N:25]=[CH:24][C:23]([N:20]3[CH2:21][CH2:22][C:17]4[CH:16]=[C:15]([C:12]5[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][CH:13]=5)[S:37][C:18]=4[C:19]3=[O:36])=[CH:28][CH:27]=2)[CH2:31][CH2:32]1)(=[O:40])[CH3:39]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 66674020HCID 66674020, compound

Product 1

HCID 66674274HCID 66674274, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Add pyridine (0.50 mL, 6.18 mmol) to a mixture of 2-(4-chloro-phenyl)-6-[6-(piperidin-4-yloxy)-pyridin-3-yl]-6H-thieno[2,3-c]pyridin-7-one, hydrochloride (0.741 g, 1.56 mmol) in dichloromethane at room temperature. After stirring for 5 min, add acetyl chloride (0.16 mL, 2.33 mmol) to the mixture and stir overnight at room temperature. Dilute the mixture with water, extract into dichloromethane (3×50 mL), then dry over sodium sulfate, filter, and concentrate. Purify the residue using silica gel flash column chromatography (1-3% methanol/dichloromethane) and concentrate on high vacuum to yield the titled compound (0.678 g, 90%). MS/ES m/z (37Cl) 483 [M+].

Workup

  1. stirringstir overnight at room temperature
  2. extractionextract into dichloromethane (3×50 mL)
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the residue
  7. concentrationconcentrate on high vacuum

Sources & evidence

ORD record
ord-03f5b0b4190f43a5993364a1e17f7848
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

Loading…