Hydrochloric Acid → 1-(5-(Benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)ethanone hydrochloride

HRID 1426104ノート

反応式

HRID 1426104 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:22]([OH:24])[CH3:23])[CH:12]=[N:13][C:14]=1[NH:15][C:16]1[S:17][CH:18]=[C:19]([CH3:21])[N:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+].[ClH:49]>ClCCl.CCOCC>[ClH:49].[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:22](=[O:24])[CH3:23])[CH:12]=[N:13][C:14]=1[NH:15][C:16]1[S:17][CH:18]=[C:19]([CH3:21])[N:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 592256651-(5-(Benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)ethanol

生成物 1

HCID 866396581-(5-(Benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)ethanone hydrochloride収率 48.3%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

1-(5-(Benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)ethanol (prepared according to Example 19; 0.128 g, 0.375 mmol) was placed in dichloromethane (5 mL). A solution of Dess-Martin periodinane (0.167 g, 0.394 mmol) in dichloromethane (7 mL) was added and the reaction mixture was stirred at room temperature for 20 minutes. 1M NaOH and ether were added, and the layers were separated. The organic layer was washed with 1M NaOH and water, then dried, filtered, and concentrated. The residue was purified by silica gel to provide the free base, which was dissolved in dichloromethane. 2M HCl was added and the solution was concentrated to afford 1-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)ethanone hydrochloride (0.068 g, 48.3% yield). 1H NMR (DMSO-d6) δ 8.62 (d, 1H), 7.73 (m, 1H), 7.60 (m, 2H), 7.42 (m, 2H), 7.35 (m, 1H), 6.79 (s, 1H), 5.36 (s, 2H), 2.57 (s, 3H), 2.30 (s, 3H). Mass spectrum (apci) m/z=340.1 (M+H-HCl).

後処理

  1. customthe layers were separated
  2. washThe organic layer was washed with 1M NaOH and water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel
  7. customto provide the free base, which
  8. concentrationthe solution was concentrated

出典と根拠

ORDレコード
ord-6f9669e40e3b402090f5ab61122c7cf7
出典データセット
uspto-grants-2015_01
特許番号
US08933077B2

反応ノート

読み込み中…