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 1821090Notes

Reaction equation

HRID 1821090 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-a2fe845b1ddc48e388aec9506ad57c7a
Source dataset
uspto-grants-2009_10
Patent number
US07605265B2

Reaction notes

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