Sodium triacetoxyborohydride → (1H-Benzoimidazol-2-ylmethyl)-(4-{[(pyrrolidin-2-ylmethyl)-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

HRID 7173

反応式

HRID 7173 の反応式
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][C@@H:9]1[CH:10]=O)=O)(C)(C)C.[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[CH2:24][N:25]([CH:35]1[C:44]2[N:43]=[CH:42][CH:41]=[CH:40][C:39]=2[CH2:38][CH2:37][CH2:36]1)[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][NH2:34])=[CH:29][CH:28]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[CH2:24][N:25]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][NH:34][CH2:10][CH:9]2[CH2:12][CH2:13][CH2:14][NH:8]2)=[CH:29][CH:28]=1)[CH:35]1[C:44]2[N:43]=[CH:42][CH:41]=[CH:40][C:39]=2[CH2:38][CH2:37][CH2:36]1

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 7009153N-(tert-Butoxycarbonyl)-D-prolinalHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine

生成物 1

HCID 22018599(1H-Benzoimidazol-2-ylmethyl)-(4-{[(pyrrolidin-2-ylmethyl)-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Using General Procedure B: To a stirred solution of N-(tert-butoxycarbonyl)-D-prolinal (0.121 g, 0.61 mmol) in dry CH2Cl2 (9 mL) was added N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.236 g, 0.59 mmol) at room temperature and the mixture stirred for 40 min. To the resultant mixture was added sodium triacetoxyborohydride (0.174 g, 0.82 mmol) and the mixture stirred overnight at room temperature. Purification and separation of the crude material by radial chromatography on a 2 mm TLC grade silica gel plate (CH2Cl2/MeOH/NH4OH, 50:1:1) afforded the more polar mono-alkylated (77 mg, 23%) and the less polar dialkylated (70 mg, 21%) products, both as white foams.

後処理

  1. stirringthe mixture stirred overnight at room temperature
  2. customPurification and separation of the crude material by radial chromatography on a 2 mm TLC grade silica gel plate (CH2Cl2/MeOH/NH4OH, 50:1:1)
  3. customafforded the more polar mono-alkylated (77 mg, 23%)

出典と根拠

ORDレコード
ord-f60b003fd2d94e8d9b9542ea7a90f1dd
出典データセット
uspto-grants-2006_08
特許番号
US07084155B2

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