Triethylamine → HCID 89649339, compound

HRID 2207595Notes

Reaction equation

HRID 2207595 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([CH3:7])[C:3]1=[O:8].[Br:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([CH:16]=O)[C:11]=1[CH3:18].[CH:19]([S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])=[O:22])=[CH2:20].[O-]S(C(F)(F)F)(=O)=O.[Ca+2].[O-]S(C(F)(F)F)(=O)=O.C(N(CC)CC)C>CO>[C:24]1([S:21]([CH:19]2[CH:16]([C:12]3[C:11]([CH3:18])=[C:10]([Br:9])[CH:15]=[CH:14][N:13]=3)[NH:1][C:2]3([CH2:6][CH2:5][N:4]([CH3:7])[C:3]3=[O:8])[CH2:20]2)(=[O:23])=[O:22])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 5

HCID 8471Triethylamine2×HCID 79664Phenyl vinyl sulfone2×HCID 2734307Methanesulfonic acid, 1,1,1-trifluoro-, calcium salt (2:1)2×HCID 457911333-Amino-1-methylpyrrolidin-2-oneHCID 722099504-Bromo-3-methyl-2-pyridinecarboxaldehyde

Product 1

HCID 89649339HCID 89649339, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of 3-amino-1-methyl-pyrrolidin-2-one (3258.49 mg, 28.55 mmol) in methanol (8 mL) was added 4-bromo-3-methyl-pyridine-2-carbaldehyde (which may be prepared as described in Description 7) (5710 mg, 28.55 mmol), phenyl vinyl sulfone (4801.68 mg, 28.55 mmol), and calcium triflate (482.74 mg, 1.43 mmol). The reaction was stirred for 5 minutes. Triethylamine (3.97 mL, 28.55 mmol) was then added [caution—slight exotherm observed], and the reaction was stirred for 15 minutes. A large amount of solid was observed to precipitate out of the reaction, this was sonicated and stirred for a further 15 minutes. The solid was then filtered off, and washed with additional methanol (approximately 10 mL). The pale cream solid was then washed with diethyl ether (10 mL), and air dried for 10 minutes to give a colourless solid, then dissolved in MeOH (8 mL), and treated with phenyl vinyl sulfone (4801.68 mg, 28.55 mmol), calcium triflate (482.74 mg, 1.43 mmol) and lastly triethylamine (3.97 mL, 28.55 mmol). The reaction mixture was then stirred at room temperature for 16 hours. The solid was filtered off, and washed with Et2O (10 mL). The solid was then air dried for 15 minutes on the sinter to afford 7-(benzene-sulfonyl)-8-(4-bromo-3-methyl-2-pyridyl)-3-methyl-3,9-diazaspiro[4.4]nonan-4-one (D8) (3520 mg, 7.58 mmol, 26.5% yield);

Workup

  1. stirringthe reaction was stirred for 15 minutes
  2. customto precipitate out of the reaction
  3. customthis was sonicated
  4. stirringstirred for a further 15 minutes
  5. filtrationThe solid was then filtered off
  6. washwashed with additional methanol (approximately 10 mL)
  7. washThe pale cream solid was then washed with diethyl ether (10 mL), and air
  8. customdried for 10 minutes
  9. customto give a colourless solid
  10. stirringThe reaction mixture was then stirred at room temperature for 16 hours
  11. filtrationThe solid was filtered off
  12. washwashed with Et2O (10 mL)
  13. customair dried for 15 minutes on the sinter

Sources & evidence

ORD record
ord-5a1b1219504f44fc84ffcc9b60000c27
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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