Triethylamine → HCID 70872539, compound

HRID 1616447Notes

Reaction equation

HRID 1616447 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[CH:15]=[C:16]([C:30]2[CH:35]=[CH:34][C:33]([CH2:36][N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[CH:32][CH:31]=2)[CH:17]=[C:18]([N:21]([CH2:28][CH3:29])[CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[C:19]=1[CH3:20])=[O:13].C(N(CC)CC)C.[S:50](Cl)([CH3:53])(=[O:52])=[O:51].[OH-].[Na+]>C(Cl)Cl.CO.O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[CH:15]=[C:16]([C:30]2[CH:35]=[CH:34][C:33]([CH2:36][N:37]3[CH2:38][CH2:39][O:40][CH2:41][CH2:42]3)=[CH:32][CH:31]=2)[CH:17]=[C:18]([N:21]([CH2:28][CH3:29])[CH:22]2[CH2:23][CH2:24][N:25]([S:50]([CH3:53])(=[O:52])=[O:51])[CH2:26][CH2:27]2)[C:19]=1[CH3:20])=[O:13]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 70872340HCID 70872340, compound

Product 1

HCID 70872539HCID 70872539, compoundYield 45.45%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To stirred solution of N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-5-(ethyl(piperidin-4-yl)amino)-4-methyl-4′-(morpholinomethyl)-[1,1′-biphenyl]-3-carboxamide (0.2 g, 0.35 mmol) in DCM (8 mL) was added triethyl amine (0.106 g, 1.04 mmol) and mesyl chloride (0.08 g, 0.69 mmol) at 0° C. The resulting reaction mixture was stirred at room temperature for 2 h. After completion, water was added to the reaction mixture and extracted with 10% MeOH/DCM. Combined organic layers were dried over sodium sulphate and concentrated under reduced pressure giving crude material which was then dissolved in methanol (10 mL) and added NaOH (0.021 g, 0.52 mmol). This mixture was stirred at room temperature for 15 h. After completion, extraction was carried out using 20% MeOH/DCM. Combined organic layers were dried over sodium sulfate, concentrated and crude material was purified by solvent washing giving the title compound (0.1 g, 45.45%).

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with 10% MeOH/DCM
  3. dry with materialCombined organic layers were dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customgiving crude material which
  6. stirringThis mixture was stirred at room temperature for 15 h
  7. extractionAfter completion, extraction
  8. dry with materialCombined organic layers were dried over sodium sulfate
  9. concentrationconcentrated
  10. customcrude material was purified by solvent
  11. washwashing

Sources & evidence

ORD record
ord-89e102041b0a4a169fdd1ca1d9fecd7d
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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