Hydrochloric Acid → HCID 67429444、化合物

HRID 1040203ノート

反応式

HRID 1040203 の反応式
[CH3:1][C:2]1([CH3:36])[C:11]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[C:22]([NH:24][C:25]4[N:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][N:26]=4)[CH:21]=[C:20]([CH3:35])[CH:19]=3)=[CH:16][N:17]=2)([OH:12])[CH2:10][CH2:9][CH2:8][C:3]21OCC[O:4]2.Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[OH:12][C:11]1([C:13]2[S:14][C:15]([C:18]3[CH:23]=[C:22]([NH:24][C:25]4[N:30]=[C:29]([C:31]([F:33])([F:34])[F:32])[CH:28]=[CH:27][N:26]=4)[CH:21]=[C:20]([CH3:35])[CH:19]=3)=[CH:16][N:17]=2)[CH2:10][CH2:9][CH2:8][C:3](=[O:4])[C:2]1([CH3:36])[CH3:1]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 67432981HCID 67432981、化合物

生成物 1

HCID 67429444HCID 67429444、化合物収率 97.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of the product of Step 1 (600 mg, 1.15 mmol) in THF (4 mL) was added HCl (6 M, 3.84 mL, 23.1 mmol). The reaction mixture was allowed to stir at room temperature for 30 min, neutralized with aqueous saturated sodium bicarbonate, and extracted with dichloromethane (3×). The combined organics were dried (sodium sulfate), filtered, concentrated, and purified by flash chromatography on silica to afford 3-hydroxy-2,2-dimethyl-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclohexanone (534 mg, 1.12 mmol) as a yellow foam. MS ESI: [M+H]+ m/z 477.1.

後処理

  1. extractionextracted with dichloromethane (3×)
  2. dry with materialThe combined organics were dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography on silica

出典と根拠

ORDレコード
ord-5c1a57609eb04f9ba7d8a2f44c7a8583
出典データセット
uspto-grants-2013_10
特許番号
US08551984B2

反応ノート

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