Potassium Carbonate → 1-{4-[6-(1h-Pyrrolo[2,3-b]pyridin-3-yl)-pyrimidin-4-yl]-[1,4]diazepan-1-yl}-ethanone

HRID 877917Notes

Reaction equation

HRID 877917 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10](S(C3C=CC(C)=CC=3)(=O)=O)[CH:9]=2)[CH:3]=1.[C:27]([N:30]1[CH2:36][CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)(=[O:29])[CH3:28].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CN(C=O)C.CO>[NH:10]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:16]2[C:8]([C:4]2[N:5]=[CH:6][N:7]=[C:2]([N:33]3[CH2:34][CH2:35][CH2:36][N:30]([C:27](=[O:29])[CH3:28])[CH2:31][CH2:32]3)[CH:3]=2)=[CH:9]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 4186202N-AcetylhomopiperazineHCID 575978283-(6-Chloro-pyrimidin-4-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 115735881-{4-[6-(1h-Pyrrolo[2,3-b]pyridin-3-yl)-pyrimidin-4-yl]-[1,4]diazepan-1-yl}-ethanoneYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 8 (0.035 g, 0.091 mmol), N-acetyl-homopiperizine (0.025 g, 0.181 mmol), excess potassium carbonate in DMF was heated at 80° C. resulting in a color change after 5 minutes. LC/MS and TLC indicated conversion to tosyl protected product after 15 minutes. 1 ml of 6N NaOH and 1 ml of methanol were added to the reaction resulting in the immediate removal the tosyl group by LC/MS (M+1=337). The reaction was partitioned between EtOAc/H2O and extracted. The crude product was purified by preparative HPLC giving 9 (0.022 g) as a clear oil in 73% yield.

Workup

  1. customresulting in a color change after 5 minutes
  2. customafter 15 minutes
  3. customresulting in the immediate removal the tosyl group by LC/MS (M+1=337)
  4. customThe reaction was partitioned between EtOAc/H2O
  5. extractionextracted
  6. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-af4c55a558fa47c78ce854bfec16c9cb
Source dataset
uspto-grants-2015_03
Patent number
US08987454B2

Reaction notes

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