Sodium triacetoxyborohydride → Methyl 2-(4-((3-(4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propylamino)methyl)phenyl)acetate

HRID 2090264ノート

反応式

HRID 2090264 の反応式
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:18])[C:8]=2[N:7]=[C:6]1[CH2:19][CH2:20][O:21][CH3:22].[CH:23]([C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]([O:34][CH3:35])=[O:33])=[CH:27][CH:26]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.C(O)(=O)C>[NH2:18][C:9]1[C:8]2[N:7]=[C:6]([CH2:19][CH2:20][O:21][CH3:22])[N:5]([CH2:4][CH2:3][CH2:2][NH:1][CH2:23][C:25]3[CH:26]=[CH:27][C:28]([CH2:31][C:32]([O:34][CH3:35])=[O:33])=[CH:29][CH:30]=3)[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

参加物

6

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 19363032Methyl 2-(4-formylphenyl)acetateHCID 223444281-(3-aminopropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine

生成物 1

HCID 68430910Methyl 2-(4-((3-(4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propylamino)methyl)phenyl)acetate収率 37.9%

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To the product from step (iv) (1.25 g) in THF (100 mL), methyl 2-(4-formylphenyl)acetate (0.818 g) was addded followed by sodium triacetoxyborohydride (0.885 g) and acetic acid (3 drops) and stirred at rt for 16 h. The reaction was quenched with water, extracted with DCM washed with sat. NaHCO3 (200 mL), dried and solvent removed. The resulting residue was dissolved in methanol and purified on SCX to give the subtitle compound (0.73 g).

後処理

  1. customThe reaction was quenched with water
  2. extractionextracted with DCM
  3. washwashed with sat. NaHCO3 (200 mL)
  4. customdried
  5. customsolvent removed
  6. dissolutionThe resulting residue was dissolved in methanol
  7. custompurified on SCX

出典と根拠

ORDレコード
ord-37498085930444ceb970faed04e5b705
出典データセット
uspto-grants-2013_05
特許番号
US08436178B2

反応ノート

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