Acetic Acid → HCID 89649623, compound

HRID 2207597Notes

Reaction equation

HRID 2207597 reaction equation
C1(S([CH:10]2[CH:20]([C:21]3[CH:26]=[C:25]([Br:27])[CH:24]=[C:23]([CH3:28])[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:27][C:25]1[CH:24]=[C:23]([CH3:28])[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)[CH:26]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 23665647Potassium tert-butoxideHCID 89649142HCID 89649142, compound

Product 1

HCID 89649623HCID 89649623, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 7-(benzenesulfonyl)-8-(4-bromo-6-methyl-2-pyridyl)-3-methyl-3,9-diazaspiro[4.4]nonan-4-one (which may be prepared as described in Description 12) in THF (20 mL) at 00° C. was added 1.7 M potassium tert-butoxide in THF (2.69 mL, 4.58 mmol) dropwise over 5 minutes. The reaction mixture was stirred at 00° C. for 1.5 hours. The reaction was quenched by the addition of acetic acid (0.26 mL, 4.58 mmol) and then the mixture was filtered, washed with dichloromethane and the filtrate concentrated at reduced pressure to give a brown gum. The product was purified by silica gel chromatography eluting with 40-100% ethyl acetate in iso-hexane to give racemic 2-(4-bromo-6-methyl-2-pyridyl)-7-methyl-1,7-diazaspiro[4.4]non-1-en-6-one a pale yellow solid (D13) (314 mg);

Workup

  1. filtrationthe mixture was filtered
  2. washwashed with dichloromethane
  3. concentrationthe filtrate concentrated at reduced pressure
  4. customto give a brown gum
  5. customThe product was purified by silica gel chromatography
  6. washeluting with 40-100% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-ca396bb344d5432e8e0f1c8dffcbf468
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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