1,1'-Carbonyldiimidazole → HCID 86616960, compound

HRID 1865878Notes

Reaction equation

HRID 1865878 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14](O)=[O:15])[CH:11]=[N:10][C:9]=2[N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:4][CH:3]=1.[C:22](N1C=CN=C1)(N1C=CN=C1)=O.[NH2:34][CH2:35][C:36]([CH:39]1[CH2:41][CH2:40]1)([OH:38])[CH3:37]>CN(C)C=O>[CH:39]1([C:36]([OH:38])([CH3:37])[CH2:35][NH:34][C:14]([C:12]2[CH:11]=[N:10][C:9]([N:17]3[CH2:18][CH2:19][CH2:22][CH2:20][CH2:21]3)=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:13]=2)=[O:15])[CH2:41][CH2:40]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 211096921-Amino-2-cyclopropylpropan-2-olHCID 67504671HCID 67504671, compound

Product 1

HCID 86616960HCID 86616960, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.050 g (0.00016 mol) 6-(4-chloro-phenyl)-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid in 2 ml dimethylformamide was added at room temperature 0.055 g (0.00032 mol) 1,1′-carbonyl-diimidazole and the mixture was stirred at room temperature for 30 min. To the resulting mixture was added 0.072 g (0.00063 mol) 1-amino-2-cyclopropyl-propan-2-ol, and the mixture was stirred at room temperature for 17 hours. The resulting mixture was partitioned between 10% aqueous citric acid and ethyl acetate. The phases were separated and the organic phase was dried over magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel using a gradient of heptane to ethyl acetate to yield 0.043 g (66% yield) of the title compound as slightly yellow oil. MS (ISP) (M+H+)=415.

Workup

  1. stirringthe mixture was stirred at room temperature for 17 hours
  2. customThe resulting mixture was partitioned between 10% aqueous citric acid and ethyl acetate
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel using a gradient of heptane to ethyl acetate

Sources & evidence

ORD record
ord-80f24d91f0a44aec93f286e5b7179cf1
Source dataset
uspto-grants-2009_12
Patent number
US07629346B2

Reaction notes

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