Morpholine, hydrochloride (1:1) → 7-[2-(2-Morpholin-4-yl-propyl)-pyridin-4-yl]-imidazo[1,2-a]pyridine

HRID 1446659

反応式

HRID 1446659 の反応式
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([CH2:16][C:17](=O)[CH3:18])[CH:11]=3)=[CH:6][C:5]=12.Cl.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C([BH3-])#N.[Na+]>CO>[N:21]1([CH:17]([CH3:18])[CH2:16][C:12]2[CH:11]=[C:10]([C:7]3[CH:8]=[CH:9][N:4]4[CH:3]=[CH:2][N:1]=[C:5]4[CH:6]=3)[CH:15]=[CH:14][N:13]=2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

参加物

5

反応物 3

HCID 197884Morpholine, hydrochloride (1:1)HCID 5003444Sodium cyanoborohydrideHCID 68544526HCID 68544526、化合物

生成物 1

HCID 685425037-[2-(2-Morpholin-4-yl-propyl)-pyridin-4-yl]-imidazo[1,2-a]pyridine収率 74%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Dissolve 1-(4-imidazo[1,2-a]pyridin-7-yl-pyridin-2-yl)-propan-2-one (3.9 g, 15.5 mmol) in methanol (400 mL) under nitrogen. Add morpholine hydrochloride (38.4 g, 20 equiv.) followed by 3 {acute over (Å)} Sieves (7.8 g, powdered and dried in a vacuum oven at 100° C. overnight). Stir five minutes then add sodium cyanoborohydride (1.0 M in THF, 28 mL, 1.8 equiv.) via syringe and stir at room temperature for 5 days. Filter to remove insoluble material, washing with methanol. Concentrate to dryness then make basic with 20% NaOH (aq) and extract with ethyl acetate. Wash organics with aqueous saturated sodium chloride then dry over MgSO4. Filter and concentrate then purify by silica gel (Ethyl Acetate→5% Methanol:DCM→10% Methanol:DCM→5% 2M NH3 in methanol:DCM→10% 2 M NH3 in Methanol:DCM) to give product as a tan solid (3.7 g, 74%). MS (ES), m/z 323 (M+1).

後処理

  1. customdried in a vacuum oven at 100° C. overnight)
  2. filtrationFilter
  3. customto remove insoluble material
  4. washwashing with methanol
  5. concentrationConcentrate to dryness
  6. extractionextract with ethyl acetate
  7. dry with materialWash organics with aqueous saturated sodium chloride then dry over MgSO4
  8. filtrationFilter
  9. concentrationconcentrate
  10. customthen purify by silica gel (Ethyl Acetate→5% Methanol:DCM→10% Methanol:DCM→5% 2M NH3 in methanol:DCM→10% 2 M NH3 in Methanol:DCM)

出典と根拠

ORDレコード
ord-c517cdeddc1b4dac838390de425b15d6
出典データセット
uspto-grants-2010_02
特許番号
US07666879B2

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