Acetic Acid → HCID 89649623、化合物

HRID 2207597ノート

反応式

HRID 2207597 の反応式
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

参加物

5

反応物 3

HCID 176Acetic AcidHCID 23665647Potassium tert-butoxideHCID 89649142HCID 89649142、化合物

生成物 1

HCID 89649623HCID 89649623、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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);

後処理

  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

出典と根拠

ORDレコード
ord-ca396bb344d5432e8e0f1c8dffcbf468
出典データセット
uspto-grants-2016_06
特許番号
US09376436B2

反応ノート

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