Acetyl chloride → 1-[8-Chloro-1-(3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-yl)-4h,6h-2,3,5,10b-tetraaza-benzo[e]azulen-5-yl]-ethanone dihydrochloride

HRID 1243576Notes

Reaction equation

HRID 1243576 reaction equation
[C:1]([Cl:4])(=[O:3])[CH3:2].[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>ClCCl>[ClH:4].[ClH:5].[Cl:5][C:6]1[CH:31]=[CH:30][C:9]2[N:10]3[C:14]([CH2:15][N:16]([C:1](=[O:3])[CH3:2])[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

4

Reactant 2

HCID 6367Acetyl chlorideHCID 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 219255551-[8-Chloro-1-(3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-yl)-4h,6h-2,3,5,10b-tetraaza-benzo[e]azulen-5-yl]-ethanone dihydrochlorideYield 83.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (0.1 ml, 1.4 mmol) was added to an ice cooled solution of the amine of example 4 (200 mg, 0.53 mmol) in dichloromethane (5 ml) and stirred at room temperature for 20 hours. Dichloromethane was evaporated off under reduced pressure and the residue 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, and the solvents evaporated under reduced pressure to give the title compound as a brown foam (110 mg).

Workup

  1. customDichloromethane was evaporated off under reduced pressure
  2. customthe residue purified by chromatography on silica gel
  3. dissolutionThe residue was dissolved in dichloromethane (2 ml)
  4. additionhydrochloric acid (1M in diethyl ether, 2 ml) was added
  5. customthe solvents evaporated under reduced pressure

Sources & evidence

ORD record
ord-bf4b3aff5c8140f6a6ebdcc32bee5724
Source dataset
uspto-grants-2006_10
Patent number
US07119088B2

Reaction notes

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