Potassium Carbonate → 3-Bromo-7-{3-[(4-methylpiperazin-1-yl)methyl]phenyl}thieno[3,2-c]pyridin-4-amine

HRID 17175Notes

Reaction equation

HRID 17175 reaction equation
[Br:1][C:2]1[C:6]2[C:7]([NH2:19])=[N:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17]Cl)[CH:12]=3)[C:5]=2[S:4][CH:3]=1.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C([O-])([O-])=[O:28].[K+].[K+]>CN(C=O)C>[NH4+:8].[OH-:28].[Br:1][C:2]1[C:6]2[C:7]([NH2:19])=[N:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][N:24]4[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]4)[CH:12]=3)[C:5]=2[S:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 18450777HCID 18450777, compound

Product 2

HCID 14923Ammonium HydroxideYield 0.1%HCID 184507763-Bromo-7-{3-[(4-methylpiperazin-1-yl)methyl]phenyl}thieno[3,2-c]pyridin-4-amineYield 129.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of example 673B (200 mg, 0.5 mmol) in DMF (2.5 mL) was treated with N-methylpiperazine (0.3 mL, 2.7 mmol) and K2CO3 (350 mg, 2.5 mmol), heated at 70° C. for 1 hour, allowed to cool to room temperature, and partitioned between water and CH2Cl2. The organic extract was dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified via silica gel chromatography eluting with 10% MeOH in CH2Cl2: 0.1% NH4OH to give 135 mg of the title compound (63% yield). MS (ESI(+)) m/e 416.8, 418.8 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. custompartitioned between water and CH2Cl2
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified via silica gel chromatography
  8. washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-e7bb4d59d42643a2a254bfb2a6e67433
Source dataset
uspto-grants-2010_06
Patent number
US07737160B2

Reaction notes

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