Triethylamine → HCID 86585883, compound

HRID 1266658Notes

Reaction equation

HRID 1266658 reaction equation
[CH2:1]([CH:8]([NH:23][C:24]([C:26]1[CH:35]=[N:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=1)=[O:25])[CH:9]([OH:22])[CH2:10][CH:11]([C:18]([NH:20][NH2:21])=[O:19])[CH2:12][CH2:13][C:14]([F:17])([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:43](N1C=CN=C1)(N1C=CN=C1)=[O:44]>O1CCCC1.C(OCC)(=O)C.CCCCCC>[CH2:1]([CH:8]([NH:23][C:24]([C:26]1[CH:35]=[N:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=1)=[O:25])[CH:9]([OH:22])[CH2:10][CH:11]([C:18]1[O:19][C:43](=[O:44])[NH:21][N:20]=1)[CH2:12][CH2:13][C:14]([F:17])([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 74990038HCID 74990038, compound

Product 1

HCID 86585883HCID 86585883, compoundYield 82.5%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of quinoxaline-2-carboxylic acid (1-benzyl-7-fluoro-4-hydrazinocarbonyl-2-hydroxy-7-methyl-octyl)-amide (62 mg, 0.129 mmol) in tetrahydrofuran (2 mL) was added triethylamine (0.018, 0.129 mmol) at 0° C. was added carbonyldiimidazole (23 mg, 0.142 mmol). The reaction was allowed to warm to ambient temperature and stirred a total of 20 hours before diluting with ethyl acetate (10 mL) and hexane (2 mL). The mixture was washed with saturated aqueous ammonium chloride, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride. The organic layer was dried over magnesium sulfate, filtered and concentrated. Chromatography on silica gel gave the title compound (54 mg, 82%).

Workup

  1. washThe mixture was washed with saturated aqueous ammonium chloride, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ea84e15ebf1549e4a1ad452c527ca01a
Source dataset
uspto-grants-2003_04
Patent number
US06548671B2

Reaction notes

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