Dimethylformamide → N-(4-methylthiazol-2-yl)-3-(pyridin-2-ylmethoxy)pyridin-2-amine dihydrochloride

HRID 1426088

反応式

HRID 1426088 の反応式
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.[ClH:15].Br[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[ClH:15].[ClH:15].[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[C:13]([O:14][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 104656162-(4-Methylthiazol-2-ylamino)pyridin-3-olHCID 219850982-(Bromomethyl)pyridine hydrochloride

生成物 1

HCID 72705823N-(4-methylthiazol-2-yl)-3-(pyridin-2-ylmethoxy)pyridin-2-amine dihydrochloride収率 142.9%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A vial was charged with 2-(4-methylthiazol-2-ylamino)pyridin-3-ol (75 mg, 0.362 mmol), 2-(bromomethyl)pyridine hydrochloride (75.4 mg, 0.362 mmol), potassium carbonate (175 mg, 1.27 mmol), and DMF (3 mL), and the reaction mixture was stirred overnight at room temperature. The reaction mixture was then poured into water and extracted with ether. The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated, and purified over silica gel (80% EtOAc in hexanes). The residue was dissolved in 1:1 CH2Cl2:MeOH, and 2M HCl in ether was added. The solution was then concentrated to afford N-(4-methylthiazol-2-yl)-3-(pyridin-2-ylmethoxy)pyridin-2-amine dihydrochloride (96 mg, 71.4% yield) as a tan solid. 1H NMR (d6-DMSO) δ 8.77 (d, 1H), 8.19 (t, 1H), 8.07 (d, 1H), 8.04 (d, 1H), 7.67 (m, 2H), 7.16 (dd, 1H), 6.87 (s, 1H), 5.53 (s, 2H), 2.33 (s, 3H). Mass spectrum (apci) m/z=299 (M+H-2HCl).

後処理

  1. extractionextracted with ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified over silica gel (80% EtOAc in hexanes)
  7. dissolutionThe residue was dissolved in 1:1 CH2Cl2
  8. additionMeOH, and 2M HCl in ether was added
  9. concentrationThe solution was then concentrated

出典と根拠

ORDレコード
ord-941a9fd9d4f3400dbad61bb496750e22
出典データセット
uspto-grants-2015_01
特許番号
US08933077B2

関連ノート

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