Diisopropylethylamine → HCID 71525480, compound

HRID 1477765Notes

Reaction equation

HRID 1477765 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([C:15]([OH:17])=O)=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=1.Cl[C:19](N(C)C)=[C:20]([CH3:22])C.Cl.[CH3:27][C:28]([CH3:36])([C:30]1[N:34]=[C:33]([CH3:35])[O:32][N:31]=1)[NH2:29].C(N(C(C)C)C(C)C)C>ClCCl.CN(C=O)C>[CH3:27][C:28]([NH:29][C:15]([C:5]1[CH:4]=[N:3][C:2]([CH:22]2[CH2:20][CH2:19]2)=[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)[N:6]=1)=[O:17])([C:30]1[N:34]=[C:33]([CH3:35])[O:32][N:31]=1)[CH3:36]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 470030731240526-27-5HCID 86682316HCID 86682316, compound

Product 1

HCID 71525480HCID 71525480, compoundYield 49.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

5-Bromo-6-(3-chloro-phenyl)-pyrazine-2-carboxylic acid (0.200 g, 638 μmol) was suspended in dichloromethane (1 mL) and 1-chloro-N,N,2-trimethylpropenylamine (98.0 mg, 97.0 μl, 734 μmol) was added dropwise at room temperature. After 30 min stirring the brown solution was added drop by drop to a solution of α,α,5-trimethyl-1,2,4-oxadiazole-3-methanamine hydrochloride (CAN 1240526-27-5; 142 mg, 797 μmol) and ethyldiisopropylamine (206 mg, 264 μl, 1.59 mmol) in DMF (1 mL) and the reaction mixture was stirred at room temperature for 30 minutes. The mixture was extracted with ethyl acetate and 1M citric acid solution; the organic phase was dried with MgSO4; filtered and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 20 g, 5% to 50% ethyl acetate in n-heptane) to give the desired product (126 mg, 45%) as white foam; MS (EI): 436.0 (M+H).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  2. extractionThe mixture was extracted with ethyl acetate and 1M citric acid solution
  3. dry with materialthe organic phase was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (silica gel, 20 g, 5% to 50% ethyl acetate in n-heptane)

Sources & evidence

ORD record
ord-c2cf52f4c5484dd4ae70a9bf0df57be1
Source dataset
uspto-grants-2016_08
Patent number
US09403808B2

Reaction notes

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