Dimethylamine → 9-{2-[1-(4-Dimethylaminomethylbenzyl)piperidin-4-yl]ethyl}-8-methoxy-2-(2-methoxyethoxy)-9H-purin-6-ylamine

HRID 1666205노트

반응식

HRID 1666205 반응식
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:33][CH3:34])[N:6]2[CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=2)[CH2:20][CH2:19]1.[CH3:35][NH:36][CH3:37].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C1COCC1>[CH3:35][N:36]([CH2:29][C:28]1[CH:31]=[CH:32][C:25]([CH2:24][N:21]2[CH2:20][CH2:19][CH:18]([CH2:17][CH2:16][N:6]3[C:5]([O:33][CH3:34])=[N:4][C:3]4[C:7]3=[N:8][C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[N:10][C:2]=4[NH2:1])[CH2:23][CH2:22]2)=[CH:26][CH:27]=1)[CH3:37]

참가 물질

6

반응물 4

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 592880284-(4-{2-[6-Amino-8-methoxy-2-(2-methoxyethoxy)purin-9-yl]ethyl}-piperidin-1-ylmethyl)benzaldehyde

생성물 1

HCID 592880309-{2-[1-(4-Dimethylaminomethylbenzyl)piperidin-4-yl]ethyl}-8-methoxy-2-(2-methoxyethoxy)-9H-purin-6-ylamine수율 87%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The compound (0.31 g, 1.66 mmol) obtained in Step (ii) was dissolved in THF (10 ml), and thereto were added at 0° C. dimethylamine (2M THF solution, 2.62 ml, 5.24 mmol) and sodium triacetoxy borohydride (0.56 g, 2.62 mmol), and the mixture was stirred at room temperature for 20 hours. The mixture was cooled to 0° C., and thereto was added a saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted three times with chloroform/ethanol=3/1. The extract was dried over magnesium sulfate, concentrated, and purified by silica gel column (chloroform/methanol/28% aqueous ammonia=100/5/0 to 100/5/1) to give the title compound (0.28 g, 0.57 mmol) as a white solid. Yield: 87%.

후처리

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionthe mixture was extracted three times with chloroform/ethanol=3/1
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel column (chloroform/methanol/28% aqueous ammonia=100/5/0 to 100/5/1)

출처 및 근거

ORD 기록
ord-3748827f543049938de508b09c604030
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044056B2

반응 노트

불러오는 중…