Acetic Acid → HCID 67061203, compound

HRID 2234556Notes

Reaction equation

HRID 2234556 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20](C=O)[CH:21]=[N:22][CH:23]=3)[CH:16]=2)[N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=1.[CH3:36][N:37]([CH3:46])[CH2:38][CH2:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.[CH3:47][C:48]([OH:50])=[O:49].[Cl:51][CH:52]([Cl:54])C>>[NH4+:11].[OH-:2].[CH3:48][OH:49].[CH2:52]([Cl:54])[Cl:51].[CH3:3][CH2:4][O:49][C:48]([CH3:47])=[O:50].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([N:43]4[CH2:44][CH2:45][N:40]([CH2:39][CH2:38][N:37]([CH3:46])[CH3:36])[CH2:41][CH2:42]4)[CH:21]=[N:22][CH:23]=3)[CH:16]=2)[NH:11][CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 27362291-(2-(Dimethylamino)ethyl)piperazineHCID 59699835HCID 59699835, compound

Product 2

HCID 22662668HCID 22662668, compoundHCID 67061203HCID 67061203, compoundYield 20%

Procedure

To a solution of 5-[3-(2-Methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridine-3-carbaldehyde (24 mg, 0.050 mmol) and dimethyl-(2-piperazin-1-yl-ethyl)-amine (10 μL, 0.065 mmol) in 1.5 ml dichloroethane was added 3 μL of AcOH. The mixture was stirred at room temperature for 30 minutes before sodium trioxyacetylborohydride (22 mg, 0.10 mmol) was added. The reaction mixture was stirred at room temperature for another 2 hours before being concentrated. The resulting residue was then dissolved in 2 ml of MeOH, to this was added 100 μL of 5N NaOH, the mixture was stirred at 60° C. for 2 hours. Solvents were removed and the residue was purified by flash silica gel chromatography using ethyl acetate and then a solvent mixture (NH4OH/MeOH/CH2Cl2/EtOAc=0.05/1/4/4) to afford [2-(4-{5-[3-(2-Methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-piperazin-1-yl)-ethyl]-dimethyl-amine (4.70 mg, 20% yield) as a white solid. MS: m/z 471 [MH+].

Workup

  1. additionwas added
  2. concentrationbefore being concentrated
  3. dissolutionThe resulting residue was then dissolved in 2 ml of MeOH
  4. additionto this was added 100 μL of 5N NaOH
  5. stirringthe mixture was stirred at 60° C. for 2 hours
  6. customSolvents were removed
  7. customthe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-d275928c046d4f76bcbf28dd54b02368
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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