1,2-Dichloroethane → HCID 178486790, compound

HRID 1639614Notes

Reaction equation

HRID 1639614 reaction equation
C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.[CH3:15][O:16][C:17]1[C:31]([O:32][CH3:33])=[CH:30][C:20]2[NH:21][C:22]([C:24]3[C:28]([NH2:29])=[CH:27][NH:26][N:25]=3)=[N:23][C:19]=2[CH:18]=1.[C:34]([N:41]1[CH2:46][CH2:45][O:44][CH:43]([C:47](O)=[O:48])[CH2:42]1)([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35]>CN(C=O)C>[CH3:33][O:32][C:31]1[C:17]([O:16][CH3:15])=[CH:18][C:19]2[NH:23][C:22]([C:24]3[C:28]([NH:29][C:47]([CH:43]4[O:44][CH2:45][CH2:46][N:41]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:42]4)=[O:48])=[CH:27][NH:26][N:25]=3)=[N:21][C:20]=2[CH:30]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 27559654-((Tert-butoxy)carbonyl)morpholine-2-carboxylic acidHCID 178486794HCID 178486794, compound

Product 1

HCID 178486790HCID 178486790, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of EDC (125 mg, 0.54 mmol) and HOAt (74 mg, 0.54 mmol) in DMF (2 ml) was added 3-(5,6-dimethoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (117 mg, 0.45 mmol) (Example 15B) and (rac)-BOC-2-carboxymorpholine (125 mg, 0.54 mmol) and the mixture stirred at room temperature overnight. The mixture was then partitioned between EtOAc and water. The organic layer was then washed successively with saturated aqueous sodium bicarbonate, brine and then dried (MgSO4). The solution was evaporated to dryness in vacuo and the residue purified by flash column chromatography [SiO2, gradient elution: EtOAc-hexanes (1:1)-EtOAc-MeOH (80:20)] to give N-[3-(5,6-dimethoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-rac-4-BOC-2-morpholine carboxamide (65 mg) as a colourless solid. (LC/MS (acidic method): Rt 2.65 min, [M+H]+ 473).

Workup

  1. customThe mixture was then partitioned between EtOAc and water
  2. washThe organic layer was then washed successively with saturated aqueous sodium bicarbonate, brine
  3. dry with materialdried (MgSO4)
  4. customThe solution was evaporated to dryness in vacuo
  5. customthe residue purified by flash column chromatography [SiO2, gradient elution: EtOAc-hexanes (1:1)-EtOAc-MeOH (80:20)]

Sources & evidence

ORD record
ord-6d4e9fd73763430985145d85a97a830e
Source dataset
uspto-grants-2012_02
Patent number
US08110573B2

Reaction notes

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