Water → 4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl morpholine-4-carboxylate

HRID 540951ノート

反応式

HRID 540951 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:7][C:8]1[C:17]2[N:18]=[C:19]([CH2:24][O:25][CH2:26][CH3:27])[N:20]([CH2:21][CH2:22][CH3:23])[C:16]=2[C:15]2[CH:14]=[C:13]([OH:28])[CH:12]=[CH:11][C:10]=2[N:9]=1.[N:29]1([C:35](Cl)=[O:36])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.O>CN(C=O)C>[N:29]1([C:35]([O:28][C:13]2[CH:12]=[CH:11][C:10]3[N:9]=[C:8]([NH2:7])[C:17]4[N:18]=[C:19]([CH2:24][O:25][CH2:26][CH3:27])[N:20]([CH2:21][CH2:22][CH3:23])[C:16]=4[C:15]=3[CH:14]=2)=[O:36])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 848104-Morpholinecarbonyl chlorideHCID 689719384-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-ol

生成物 1

HCID 588336324-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl morpholine-4-carboxylate収率 88.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Cesium carbonate (1.62 g, 5.00 mmol) was added to a solution of 4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-ol (500 mg, 1.66 mmol, prepared in Parts A and B of Example 566) in anhydrous DMF (30 mL). The reaction was stirred for ten minutes, and 4-morpholinecarbonyl chloride (275 mg, 1.83 g) was then added. The reaction was stirred overnight at ambient temperature and poured into deionized water (300 mL). The resulting mixture was stirred for one hour and then extracted with chloroform (3×100 mL). The combined organic fractions were concentrated under reduced pressure, and the resulting solid was purified by chromatography on a HORIZON HPFC system (silica cartridge, eluting with a gradient of 0-20% CMA in chloroform). The resulting solid was recrystallized from acetonitrile and dried under vacuum to yield 606 mg of 4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl morpholine-4-carboxylate as a white, crystalline solid, mp 193-196° C. Anal. calcd for C21H27N5O4: C, 61.00; H, 6.58; N, 16.94. Found: C, 61.01; H, 6.51; N, 17.21.

後処理

  1. stirringThe reaction was stirred overnight at ambient temperature
  2. stirringThe resulting mixture was stirred for one hour
  3. extractionextracted with chloroform (3×100 mL)
  4. concentrationThe combined organic fractions were concentrated under reduced pressure
  5. customthe resulting solid was purified by chromatography on a HORIZON HPFC system (silica cartridge
  6. washeluting with a gradient of 0-20% CMA in chloroform)
  7. customThe resulting solid was recrystallized from acetonitrile
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-8947f08c30ad423f8233e7b9a88dc05e
出典データセット
uspto-grants-2014_10
特許番号
US08871782B2

反応ノート

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