HCID 9888789, compound → HCID 9930458, compound

HRID 2300896Notes

Reaction equation

HRID 2300896 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:25]5[N:26]=[N:27][C:28](Cl)=[CH:29][CH:30]=5)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)C.C1COCC1.[Pd]>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:25]5[N:26]=[N:27][CH:28]=[CH:29][CH:30]=5)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 9888789HCID 9888789, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9930458HCID 9930458, compoundYield 9.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-[(S)-1-phenylethylamino]-4-[5-(6-chloropyridazin-3-yl)-benzimidazol-1-yl]pyrimidine (24.0 mg) was dissolved in 2 mL ethanol and 2 mL THF. Added 10%Pd/C (23.0 mg), fitted the system with a balloon of hydrogen and purged 3 times, and the system was left stirring for 20 h at room temperature. No apparent progress at this point so 1-drop of glacial acetic acid was added and refitted with the balloon and purged. Stirred approximately 20 h longer then filtered off the catalyst, the solvent was removed and the residue purified by preparative thin layer chromatography (1:1 hexanes:acetone then another in 90:10 CH2Cl2:MeOH to yield 2.0 mg of the title compound. 1H NMR (500 MHz, CDCl3, partial): δ 9.20 (dd, J=1.5, 4.9 Hz, 1H); 8.54 (br s, IH); 8.44 (d, J=5.3 Hz, 1H); 8.42 (s, 1H); 8.23 (br s, 1H); 7.97 (dd, J=1.5, 8.5 Hz, 1H); 7.59 (dd, J=4.9, 8.6 Hz, 1H); 7.47 (d, J=7.3 Hz, 2H); 7.42 (t, J=7.5 Hz, 2H); 6.82 (d, J=5.3 Hz, 1H); 1.66 (d, J=6.9 Hz, 3H). Mass spectrum (ESI) 394.4 (M+1).

Workup

  1. custompurged 3 times
  2. waitthe system was left
  3. additionNo apparent progress at this point so 1-drop of glacial acetic acid was added
  4. custompurged
  5. stirringStirred approximately 20 h longer
  6. filtrationfiltered off the catalyst
  7. customthe solvent was removed
  8. customthe residue purified by preparative thin layer chromatography (1:1 hexanes

Sources & evidence

ORD record
ord-c5496c19238042b0a1c78d9b125ebb71
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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