Water → HCID 21105532, compound

HRID 1354734Notes

Reaction equation

HRID 1354734 reaction equation
[OH-].[K+].[CH3:3][N:4]([CH3:26])[CH:5]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:25])[C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[N:20][CH:19]=3)=[CH:12][CH:11]=2)[CH2:6]1.Br[CH2:28][CH2:29][CH2:30][CH3:31].O>CS(C)=O.C(OCC)(=O)C>[CH2:28]([O:24][C:21]1[CH:22]=[CH:23][C:18]([C:17]([NH:16][C:13]2[CH:12]=[CH:11][C:10]([N:7]3[CH2:8][CH2:9][CH:5]([N:4]([CH3:26])[CH3:3])[CH2:6]3)=[CH:15][CH:14]=2)=[O:25])=[CH:19][N:20]=1)[CH2:29][CH2:30][CH3:31]

Participants

7

Reactant 4

HCID 962WaterHCID 8002Butyl bromideHCID 14797Potassium HydroxideHCID 178482923HCID 178482923, compound

Product 1

HCID 21105532HCID 21105532, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.1 g of potassium hydroxide in 1 ml of DMSO was stirred at room temperature for 10 minutes and then 0.1 g of N-[4-(3-dimethylaminopyrrolidin-1-yl)-phenyl]-6-hydroxynicotinamide was added. The reaction solution was stirred for 10 minutes and then 0.084 g of 1-bromobutane was added. The mixture was stirred at room temperature overnight. After addition of water and ethyl acetate, the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate, concentrated in vacuo and purified by preparative HPLC. This resulted in the product with the molecular weight of 382.24 (C22H30N4O2); MS (ESI): 383 (M+H+) as hydrotrifluoroacetate.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. extractionthe aqueous phase was extracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified by preparative HPLC
  6. customThis resulted in the product with the molecular weight of 382.24 (C22H30N4O2)

Sources & evidence

ORD record
ord-983ba3ff75c44cd689364aa9b0028767
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

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