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

HRID 2090268노트

반응식

HRID 2090268 반응식
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:31][CH2:32][O:33][CH3:34])[N:14]([CH2:15][CH2:16][CH2:17][NH:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:22][CH:21]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.Cl.Cl[CH2:37][CH2:38][CH2:39][N:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1.C([O-])([O-])=O.[K+].[K+].[I-].[Na+]>CC#N>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:31][CH2:32][O:33][CH3:34])[N:14]([CH2:15][CH2:16][CH2:17][N:18]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:24][CH:25]=3)[CH2:37][CH2:38][CH2:39][N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 122962834-(3-Chloropropyl)morpholinium chlorideHCID 68430910Methyl 2-(4-((3-(4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propylamino)methyl)phenyl)acetate

생성물 1

HCID 25107233Methyl 2-(4-(((3-(4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propyl)(3-morpholinopropyl)amino)methyl)phenyl)acetate수율 6.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

The product from step (v) of example 29 (360 mg, 0.78 mmol) was dissolved in MeCN (10 mL) and 4-(3-chloropropyl)morpholine hydrochloride (187 mg, 0.94 mmol) added at rt. Anhydrous K2CO3 (323 mg, 2.34 mmol) and sodium iodide (117 mg, 0.78 mmol) were added. The mixture was refluxed for 15 h. After cooling to room temperature, the crude product was purified by RPHPLC and the resulting residue was triturated with diethyl ether:EtOAc (5:1) at 0° C. The suspension was filtered to afford the title compound as a pale yellow solid (31 mg).

후처리

  1. temperatureThe mixture was refluxed for 15 h
  2. customthe crude product was purified by RPHPLC
  3. customthe resulting residue was triturated with diethyl ether:EtOAc (5:1) at 0° C
  4. filtrationThe suspension was filtered

출처 및 근거

ORD 기록
ord-1e5ec2fba0264ad7a84425e864870881
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436178B2

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