Acetone → 8-Chloro-5-isopropyl-1-(3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-yl)-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene trihydrochloride

HRID 2118028Notes

Reaction equation

HRID 2118028 reaction equation
[CH3:1][C:2]([CH3:4])=O.[Cl:5][C:6]1[CH:31]=[CH:30][C:9]2[N:10]3[C:14]([CH2:15][NH:16][CH2:17][C:8]=2[CH:7]=1)=[N:13][N:12]=[C:11]3[CH:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[ClH:5].[ClH:5].[ClH:5].[Cl:5][C:6]1[CH:31]=[CH:30][C:9]2[N:10]3[C:14]([CH2:15][N:16]([CH:2]([CH3:4])[CH3:1])[CH2:17][C:8]=2[CH:7]=1)=[N:13][N:12]=[C:11]3[CH:18]1[CH2:19][CH2:20][N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 113264888-Chloro-1-(3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-yl)-5,6-dihydro4h-2,3,5,10b-tetraaza-benzo[e]azulene

Product 1

HCID 219255448-Chloro-5-isopropyl-1-(3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-yl)-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene trihydrochlorideYield 228.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetone (0.1 ml, 1.36 mmol) was added to a solution of the amine of example 4 (200 mg, 0.53 mmol) in dichloromethane (5 ml). The mixture was stirred at room temperature for 0.25 hours before sodium triacetoxyborohydride (500 mg, 2.4 mmol) was added, and the reaction mixture stirred for a further 18 hours. The reaction mixture was partitioned between 2N aqueous sodium hydroxide solution (10 ml) and dichloromethane (10 ml). The organic layer was evaporated under reduced pressure and purified by chromatography on silica gel using methanol in dichloromethane (5:95) as eluant. The residue was dissolved in dichloromethane (2 ml) and hydrochloric acid (1M in diethyl ether, 2 ml) was added. The solvent was evaporated under reduced pressure to give the title compound as a brown foam (161 mg).

Workup

  1. additionwas added
  2. customThe reaction mixture was partitioned between 2N aqueous sodium hydroxide solution (10 ml) and dichloromethane (10 ml)
  3. customThe organic layer was evaporated under reduced pressure
  4. custompurified by chromatography on silica gel
  5. dissolutionThe residue was dissolved in dichloromethane (2 ml)
  6. additionhydrochloric acid (1M in diethyl ether, 2 ml) was added
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fc6d6fa60ad546b487da1f65958d4d58
Source dataset
uspto-grants-2008_10
Patent number
US07442795B2

Reaction notes

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