Acetic Acid → HCID 89649321, compound

HRID 2207596Notes

Reaction equation

HRID 2207596 reaction equation
C1(S([CH:10]2[CH:20]([C:21]3[C:26]([CH3:27])=[C:25]([Br:28])[CH:24]=[CH:23][N:22]=3)[NH:19][C:12]3([CH2:16][CH2:15][N:14]([CH3:17])[C:13]3=[O:18])[CH2:11]2)(=O)=O)C=CC=CC=1.CC(C)([O-])C.[K+].C(O)(=O)C>C1COCC1>[Br:28][C:25]1[CH:24]=[CH:23][N:22]=[C:21]([C:20]2[CH2:10][CH2:11][C:12]3([CH2:16][CH2:15][N:14]([CH3:17])[C:13]3=[O:18])[N:19]=2)[C:26]=1[CH3:27]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 23665647Potassium tert-butoxide2×HCID 89649339HCID 89649339, compound

Product 1

HCID 89649321HCID 89649321, compoundYield 58.063%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cooled solution of 7-(benzenesulfonyl)-8-(4-bromo-3-methyl-2-pyridyl)-3-methyl-3,9-diazaspiro[4.4]nonan-4-one (which may be prepared as described in Description 8) (3500 mg, 7.54 mmol) in THF (5 mL) was added potassium tert-butoxide (1691 mg, 15.07 mmol) and the reaction was stirred for 1 hour. Additional KOtBu (1.7 g, 15.1 mmol) was added and the reaction was stirred at 00° C. for 1 hour, and allowed to warm to room temperature overnight. The reaction was quenched by addition of acetic acid (3.45 mL, 60.3 mmol), concentrated in vacuo and loaded onto a silica column (100 g SNAP). Elution using EtOAc gave 2-(4-bromo-3-methyl-2-pyridyl)-7-methyl-1,7-diazaspiro[4.4]non-1-en-6-one (1410 mg, 4.3762 mmol, 58.063% yield) as a pale yellow crystalline solid;

Workup

  1. stirringthe reaction was stirred at 00° C
  2. waitfor 1 hour
  3. concentrationconcentrated in vacuo
  4. washElution

Sources & evidence

ORD record
ord-1998c1aefb104913b4fb53b3e16707a4
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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