2-Methanesulfonyl-4-[benzimidazol-1-yl]pyrimidine → HCID 9803404, compound

HRID 2268968Notes

Reaction equation

HRID 2268968 reaction equation
CS([C:5]1[N:10]=[C:9]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[CH2:20]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([CH2:36][NH2:37])[CH2:32][CH2:31]1)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C.C1(C)C=CC=CC=1.CCOC(C)=O>[CH2:20]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([CH2:36][NH:37][C:5]2[N:10]=[C:9]([N:11]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[N:13]=[CH:12]3)[CH:8]=[CH:7][N:6]=2)[CH2:32][CH2:31]1)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 155496402-Methanesulfonyl-4-[benzimidazol-1-yl]pyrimidineHCID 219554994-Aminomethyl-1-N-Cbz-piperidine

Product 1

HCID 9803404HCID 9803404, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21735183Dimethylformamide tolueneSolvent

Conditions

Temperature
100 °C

Procedure

2-Methanesulfonyl-4-[benzimidazol-1-yl]pyrimidine (EXAMPLE 1) (115 mg, 0.42 mnmol) and 1-Benzyloxycarbonyl-4-(aminomethyl)piperidine (122 mg, 0.49 mmol) were dissolved in DMF-toluene (1:1, 5 mL), and the mixture was heated at 100° C. for 5 h. After cooling, the mixture was diluted with EtOAc and washed with H2O to remove DMF followed by brine. The organic extract was dried over Na2SO4, and the solvent was removed under reduced pressure to give 105 mg of the title compound. Partial 1H NMR (500 MHz, CDCl3): δ 8.61 (s, 1H); 8.38 (br s, 1H); 8.18 (m, 1H); 7.85 (m, 1H); 7.4-7.28 (m, 7H); 6.79 (d, J=5.5 Hz); 5.12 (s, 2H); 4.22 (br s, 2H); 3.43 (m, 1H); 2.78 (br s, 2H).

Workup

  1. temperatureAfter cooling
  2. washwashed with H2O
  3. customto remove DMF
  4. extractionThe organic extract
  5. dry with materialwas dried over Na2SO4
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f1120970267346bc97b53ba6a176902c
Source dataset
uspto-grants-2001_12
Patent number
US06329380B1

Reaction notes

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