Potassium Carbonate → HCID 178519933, compound

HRID 1984304Notes

Reaction equation

HRID 1984304 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7]([C:9](Cl)(Cl)Cl)=[N:8][C:4]=2[CH:3]=1.C([O-])([O-])=[O:16].[K+].[K+].[NH:21]1[CH2:26][CH2:25][CH2:24][C@@H:23]2[CH2:27][NH:28][CH2:29][C@H:22]12>CC#N.O>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7]([C:9]([N:28]3[CH2:27][C@@H:23]4[C@@H:22]([NH:21][CH2:26][CH2:25][CH2:24]4)[CH2:29]3)=[O:16])=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1515156(4aR,7aR)-Octahydro-1H-pyrrolo(3,4-b)pyridineHCID 178477904HCID 178477904, compound

Product 1

HCID 178519933HCID 178519933, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a suspension of 5-chloro-2-trichloromethyl-1H-benzoimidazole (30 mg, 0.11 mmol) and K2CO3 (46 mg, 0.33 mmol) in CH3CN/H2O (10:1, 3 mL) was added cis-octahydro-pyrrolo[3,4-b]pyridine (28 mg, 0.22 mmol). After 1 h at 100° C., the mixture was filtered and extracted with CH2Cl2. The organic layer was dried (Na2SO4) and concentrated to give a yellow oil, which was purified by FCC to give a brown solid (14 mg, 40%). MS (ESI): mass calcd. for C15H17ClN4O, 304.11; m/z found, 305.4 [M+H]+. 1H NMR (mixture of rotamers; MeOD): 7.70-7.58 (m, 2H), 7.35-7.25 (m, 1H), 4.43-4.28 (m, 0.6H), 4.19-4.09 (m, 0.6H), 3.77-3.69 (m, 1H), 3.46-3.40 (m, 0.3H), 3.38-3.33 (m, 0.3H), 3.33-3.28 (m, 2H), 3.04-2.82 (m, 1.5H), 2.71-2.53 (m, 1H), 2.50-2.31 (m, 1.5H), 1.95-1.43 (m, 4H).

Workup

  1. filtrationthe mixture was filtered
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customto give a yellow oil, which
  6. customwas purified by FCC

Sources & evidence

ORD record
ord-0eab7cca3ec14ac08f641467cb61a747
Source dataset
uspto-grants-2009_06
Patent number
US07544698B2

Reaction notes

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