Sodium Bicarbonate → 6-[3-(6-Chloro-1,2,3,4-tetrahydro-acridin-9-ylamino)-propylamino]-5,6,7,8-tetrahydro-1H-quinolin-2-one

HRID 1821090ノート

反応式

HRID 1821090 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]([NH:16][CH2:17][CH2:18][CH2:19][NH2:20])=[C:11]1[C:6]([CH2:7][CH2:8][CH2:9][CH2:10]1)=[N:5]2.[NH:21]1[C:30]2[CH2:29][CH2:28][C:27](=O)[CH2:26][C:25]=2[CH:24]=[CH:23][C:22]1=[O:32].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]([NH:16][CH2:17][CH2:18][CH2:19][NH:20][CH:27]1[CH2:28][CH2:29][C:30]3[NH:21][C:22](=[O:32])[CH:23]=[CH:24][C:25]=3[CH2:26]1)=[C:11]1[C:6]([CH2:7][CH2:8][CH2:9][CH2:10]1)=[N:5]2

参加物

7

反応物 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 23645224N-(3-aminopropyl)-6-chloro-1,2,3,4-tetrahydroacridin-9-amineHCID 543097987,8-Dihydroquinoline-2,6(1H,5H)-dione

生成物 1

HCID 249898316-[3-(6-Chloro-1,2,3,4-tetrahydro-acridin-9-ylamino)-propylamino]-5,6,7,8-tetrahydro-1H-quinolin-2-one収率 37%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

To a mixture of N1-(6-Chloro-1,2,3,4-tetrahydro-acridin-9-yl)-propane-1,3-diamine (50 mg, 0.17 mmoL), 1,5,7,8-Tetrahydro-quinoline-2,6-dione (31 mg, 0.19 mmoL) in 5 mL methylene chloride, was added sodium triacetoxyborohydride (110 mg, 0.52 mmoL) and a catalytic amount of acetic acid. After stiring at room temperature for 24 h, the reaction was stopped by adding saturated sodium bicarbonate. The mixture was extracted with methylene chloride three times. The combined methylene chloride extract was dried, filtered and concentrated. Purification by column chromatography on silica gel column with 10% MeOH/1% ammonium hydroxide in methylene chloride provided the desired product (27.6 mg, 0.063 mmoL, 37%).

後処理

  1. extractionThe mixture was extracted with methylene chloride three times
  2. extractionThe combined methylene chloride extract
  3. customwas dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel column with 10% MeOH/1% ammonium hydroxide in methylene chloride

出典と根拠

ORDレコード
ord-a2fe845b1ddc48e388aec9506ad57c7a
出典データセット
uspto-grants-2009_10
特許番号
US07605265B2

反応ノート

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