Acetic Acid → HCID 89649623, 화합물

HRID 2207597노트

반응식

HRID 2207597 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 89649623HCID 89649623, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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);

후처리

  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

출처 및 근거

ORD 기록
ord-ca396bb344d5432e8e0f1c8dffcbf468
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376436B2

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