Sodium Bicarbonate → 2-{[[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-4,5,6,7-tetrahydro-benzoimidazole-1-sulfonic acid dimethylamide

HRID 1624287노트

반응식

HRID 1624287 반응식
[CH3:1][N:2]([CH3:17])[S:3]([N:6]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[N:8]=[C:7]1[CH:15]=O)(=[O:5])=[O:4].[N:18]1[C:27]2[CH:26]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][N:33]3[C:41](=[O:42])[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:34]3=[O:43])[CH2:25][CH2:24][CH2:23][C:22]=2[CH:21]=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][N:2]([CH3:17])[S:3]([N:6]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[N:8]=[C:7]1[CH2:15][N:28]([CH2:29][CH2:30][CH2:31][CH2:32][N:33]1[C:34](=[O:43])[C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:41]1=[O:42])[CH:26]1[C:27]2[N:18]=[CH:19][CH:20]=[CH:21][C:22]=2[CH2:23][CH2:24][CH2:25]1)(=[O:5])=[O:4]

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 589971372-[4-(5,6,7,8-Tetrahydroquinolin-8-ylamino)-butyl]-isoindole-1,3-dioneHCID 865903112-Formyl-4,5,6,7-tetrahydro-benzoimidazole-1-sulfonic acid dimethylamide

생성물 1

HCID 691783352-{[[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-4,5,6,7-tetrahydro-benzoimidazole-1-sulfonic acid dimethylamide수율 59.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-formyl-4,5,6,7-tetrahydro-benzoimidazole-1-sulfonic acid dimethylamide (0.3991 g, 1.5 mmol) and 2-[4-(5,6,7,8-tetrahydro-quinolin-8-ylamino)-butyl]-isoindole-1,3-dione (0.4424 g, 1.3 mmol) in CH2Cl2 (13 mL) was added sodium triacetoxyborohydride (0.5539 g, 2.6 mmol), and the reaction stirred at room temperature for 22 hours. Saturated NaHCO3 (20 mL) was added and the aqueous phase was extracted with CH2Cl2 (2×100 mL), and the combined organic extracts were washed with brine (1×75 mL), dried (NaSO4), and concentrated. Purification of the crude material by column chromatography on silica gel (33:1:1 CH2Cl2—MeOH—NH4OH) provided 0.4564 g (52%) of 2-{[[4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-4,5,6,7-tetrahydro-benzoimidazole-1-sulfonic acid dimethylamide as a yellow foam. 1H NMR (CDCl3) δ 1.28 (t, 2H, J=9 Hz), 1.49-1.52 (m, 2H), 1.74-1.81 (m, 6H), 1.91-2.00 (m, 1H), 2.11-2.20 (m, 1H), 2.50-2.73 (m, 7H), 2.92 (s, 2H), 2.95 (s, 4H), 3.52-3.57 (m, 2H), 4.17-4.22 (m, 2H), 4.32-4.37 (m, 1H), 4.81 (s, 1H), 6.95-6.98 (m, 1H), 7.27-7.28 (m, 1H), 7.68-7.70 (m, 2H), 7.79-7.82 (m, 2H), 8.32 (d, 1H, J=3 Hz).

후처리

  1. extractionthe aqueous phase was extracted with CH2Cl2 (2×100 mL)
  2. washthe combined organic extracts were washed with brine (1×75 mL)
  3. dry with materialdried (NaSO4)
  4. concentrationconcentrated
  5. customPurification of the crude material by column chromatography on silica gel (33:1:1 CH2Cl2—MeOH—NH4OH)

출처 및 근거

ORD 기록
ord-c94c015ce32947e3a568d2cb673359ae
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778967B2

반응 노트

불러오는 중…