1,2-Dichloroethane → HCID 178486790, compound

HRID 1946252Notes

Reaction equation

HRID 1946252 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-4994447537ec44d1a6a086c6d221a126
Source dataset
uspto-grants-2013_03
Patent number
US08399442B2

Reaction notes

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