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 1624287ノート

反応式

HRID 1624287 の反応式
[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]

参加物

6

反応物 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

生成物 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 dimethylamide収率 59.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c94c015ce32947e3a568d2cb673359ae
出典データセット
uspto-grants-2014_07
特許番号
US08778967B2

反応ノート

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