1,1'-Carbonyldiimidazole → HCID 11408251, compound

HRID 1987319Notes

Reaction equation

HRID 1987319 reaction equation
S(O)(O)(=O)=O.[NH2:6][C:7]1[NH:8][CH:9]=[CH:10][N:11]=1.[C:12](N1C=CN=C1)(N1C=CN=C1)=[O:13].CCN(C(C)C)C(C)C.[CH3:33][C:34]1[C:35]([C@@H:40]2[CH2:45][CH2:44][CH2:43][C@H:42]([C:46]3[C:51]([CH3:52])=[CH:50][CH:49]=[CH:48][N:47]=3)[N:41]2[CH2:53][CH2:54][CH2:55][CH2:56][NH2:57])=[N:36][CH:37]=[CH:38][CH:39]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:52][C:51]1[C:46]([C@@H:42]2[CH2:43][CH2:44][CH2:45][C@H:40]([C:35]3[C:34]([CH3:33])=[CH:39][CH:38]=[CH:37][N:36]=3)[N:41]2[CH2:53][CH2:54][CH2:55][CH2:56][NH:57][C:12]([NH:6][C:7]2[NH:8][CH:9]=[CH:10][N:11]=2)=[O:13])=[N:47][CH:48]=[CH:49][CH:50]=1

Participants

7

Reactant 5

HCID 682631,1'-CarbonyldiimidazoleHCID 81531Diisopropylethylamine2×HCID 135136Bis(2-amino-1H-imidazole) sulphateHCID 516892Sodium BicarbonateHCID 9949753HCID 9949753, compound

Product 1

HCID 11408251HCID 11408251, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 2-aminoimidazole sulfate (0.100 g, 0.757 mmol), 1,1′-carbonyldiimidazole (0.129 g, 0.796 mmol) and DIPEA (0.293 g, 2.27 mmol) in CH2Cl2 (10 mL) was stirred for 5 h, and then the solvent was removed. The residue was dissolved in DMF (6 mL), and 4-((2′S,6′R)-3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-yl)-butylamine (0.130 g, 0.384 mmol) and DIPEA (0.293 g, 2.27 mmol) were added. The mixture was heated at 75° C. for 16 h, and then cooled to room temperature. Saturated aqueous NaHCO3 (20 mL) was added, and the mixture was extracted with CH2Cl2 (3×30 mL). The extracts were combined and dried over Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (100:5:2 CH2Cl2/CH3OH/NH4OH), affording a pale yellow solid (0.115 g, 67%) after precipitation from CH2Cl2/hexanes by evaporation under vacuum. 1H NMR(CDCl3) δ 0.70-0.85 (m, 4H), 1.46-1.66 (m, 3H), 1.90-2.00 (m, 2H), 2.15-2.19 (m, 2H), 2.41 (s, 6H), 2.53-2.70 (m, 1H), 2.75-2.83 (m, 2H), 3.95-4.00 (m, 2H), 6.69 (s, 2H), 6.90-7.02 (m, 2H), 7.30-7.40 (m, 2H), 8.34-8.42 (m, 2H); 13C NMR(CDCl3) δ 18.96, 22.82, 25.22, 27.67, 31.30, 39.41, 50.56, 63.61, 122.03, 131.12, 138.63, 144.22, 146.85, 155.71, 160.40. ES-MS m/z 448 (M+H). Anal. Calcd. for C25H33N7O.0.1CH2Cl2.0.1C6H14: C, 66.43; H, 7.50; N, 21.10. Found: C, 66.41; H, 7.46; N, 20.87.

Workup

  1. customthe solvent was removed
  2. dissolutionThe residue was dissolved in DMF (6 mL)
  3. temperaturecooled to room temperature
  4. extractionthe mixture was extracted with CH2Cl2 (3×30 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration the solvent
  7. customwas removed by evaporation under vacuum
  8. customthe residue was purified by flash chromatography on a silica gel column (100:5:2 CH2Cl2/CH3OH/NH4OH)

Sources & evidence

ORD record
ord-6c496929c99142b8a2c20407a3cf7e77
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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