1,1'-Carbonyldiimidazole → HCID 86696618, compound

HRID 717162Notes

Reaction equation

HRID 717162 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)C(C)C)(C)C.[Br:38][C:39]1[C:40]([NH2:46])=[N:41][CH:42]=[C:43]([Br:45])[N:44]=1>CN(C)C=O.ClCCl>[Br:38][C:39]1[C:40]([NH:46][C:14]([CH:9]2[CH2:10][O:11][CH2:12][CH2:13][N:8]2[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:16])=[N:41][CH:42]=[C:43]([Br:45])[N:44]=1

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 6200042-Amino-3,5-dibromopyrazineHCID 27601334-(tert-Butoxycarbonyl)morpholine-3-carboxylic acid

Product 1

HCID 86696618HCID 86696618, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-(tert-butoxycarbonyl)morpholine-3-carboxylic acid (1.500 g, 6.49 mmol) and 1,1′-carbonyldiimidazole (1.578 g, 9.73 mmol) in N,N-dimethylformamide (2 mL) and dichloromethane (6 mL) was stirred 4.5 h at room temperature under nitrogen. N,N-Diisopropylethylamine (2.260 mL, 12.97 mmol) was added followed by 3,5-dibromopyrazin-2-amine (3.28 g, 12.97 mmol). The resulting mixture was stirred and heated at 50° C. under a reflux condenser under nitrogen for 2 d. The resulting mixture was concentrated under reduced pressure. The residue was diluted with water and extracted 3 times with ethyl acetate. The combined organics were washed with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified using flash chromatography (20-30-50% ethyl acetate in hexanes) to give the desired product (2.136 g, 4.58 mmol, 71% yield) as a slightly yellow foam-solid. MS (ESI) m/z 467 [M+1]+.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted 3 times with ethyl acetate
  4. washThe combined organics were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified

Sources & evidence

ORD record
ord-9ca9ed44be20434da51b3687834a9c31
Source dataset
uspto-grants-2015_11
Patent number
US09193692B2

Reaction notes

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