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

HRID 2090264노트

반응식

HRID 2090264 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-37498085930444ceb970faed04e5b705
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436178B2

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