Diisopropylethylamine → HCID 86677177, compound

HRID 929352Notes

Reaction equation

HRID 929352 reaction equation
CC[N:3]([CH:7](C)C)C(C)C.[Cl:10][C:11]1[CH:12]=[N:13][C:14]2[C:19]([N:20]=1)=[CH:18][C:17]([C:21](Cl)=[O:22])=[CH:16][CH:15]=2.ClC1C=NC2C(=CC=C([C:35](Cl)=[O:36])C=2)N=1>C(Cl)Cl>[Cl:10][C:11]1[CH:12]=[N:13][C:14]2[C:19]([N:20]=1)=[CH:18][C:17]([C:21]([N:3]([O:36][CH3:35])[CH3:7])=[O:22])=[CH:16][CH:15]=2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 20228931HCID 20228931, compoundHCID 538470992-Chloro-6-quinoxalinecarbonyl chloride

Product 1

HCID 86677177HCID 86677177, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of O, N-dimethyl-hydroxylamine hydrochloride salt (29 g, 0.30 mol, 1.1 eq) and DIEA (182 mL, 1.08 mol, 4.0 eq) in DCM (300 mL) was added the mixture of 3-chloro-quinoxaline-6-carbonyl chloride and 2-chloro-quinoxaline-6-carbonyl chloride (52 g, 0.27 mol, 1.0 eq) at 0° C. The mixture was stirred at rt overnight, then concentrated. The resulting residue was washed with water (300 mL×2) and extracted with EA (300 mL×2). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The resulting solid was triturated with EA/PE =1/1 (300 mL) to afford 3-chloro-N-methoxy-N-methylquinoxaline-6-carboxamide (16.5 g, 24.3%).

Workup

  1. concentrationconcentrated
  2. washThe resulting residue was washed with water (300 mL×2)
  3. extractionextracted with EA (300 mL×2)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting solid was triturated with EA/PE =1/1 (300 mL)

Sources & evidence

ORD record
ord-7dd27f32369a4b31ba39c2fb25a80c79
Source dataset
uspto-grants-2016_03
Patent number
US09295671B2

Reaction notes

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