1,1'-Carbonyldiimidazole → HCID 178461356, compound

HRID 1826919Notes

Reaction equation

HRID 1826919 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([OH:14])=O)[CH:6]=[N:5]2.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:28][C@H:29]1[CH2:34][CH2:33][C@H:32]([NH2:35])[CH2:31][CH2:30]1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH3:28][C@H:29]1[CH2:34][CH2:33][C@H:32]([NH:35][C:12]([C:7]2[CH:6]=[N:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=3)[N:8]=2)=[O:14])[CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 221364266-Fluoroquinoxaline-2-carboxylic acidHCID 178461307HCID 178461307, compound

Product 1

HCID 178461356HCID 178461356, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-fluoroquinoxaline-2-carboxylic acid (35 mg, 0.18 mmol) in dimethylformamide (4 mL) was treated with 1,1′-carbonyldiimidazole (29 mg, 0.18 mmol) and the reaction stirred for 16 hours at ambient temperature. After this time the reaction mixture was treated with trans-4-methylcyclohexylamine hydrochloride (27 mg, 0.18 mmol) and N,N-diisopropylethylamine (0.05 mL, 0.29 mmol) and the reaction stirred 2 hours at ambient temperature. The solvent was evaporated to a solid (700 mg). The solid was dissolved in chloroform (10 mL) and added to diethyl ether (30 mL) The organic solution was washed with water (1×25 mL) and brine. The remaining organic solution was dried over anhydrous MgSO4, filtered, and concentrated to a solid (35 mg) HPLC (10 micron silica, 250×20 mm i.d.) of this material using a gradient of chloroform to 10% ethanol (in chloroform) afforded 20 mg (39%) of 434:

Workup

  1. stirringthe reaction stirred 2 hours at ambient temperature
  2. customThe solvent was evaporated to a solid (700 mg)
  3. dissolutionThe solid was dissolved in chloroform (10 mL)
  4. additionadded to diethyl ether (30 mL) The organic solution
  5. washwas washed with water (1×25 mL) and brine
  6. dry with materialThe remaining organic solution was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to a solid (35 mg) HPLC (10 micron silica, 250×20 mm i.d.) of this material

Sources & evidence

ORD record
ord-b60fb3c6aedb4020a14c467b021a6be7
Source dataset
uspto-grants-2006_05
Patent number
US07053104B2

Reaction notes

Loading…