Triethylamine → HCID 57330211, compound

HRID 2283243Notes

Reaction equation

HRID 2283243 reaction equation
C[C:2]1[N:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([C:14]([OH:16])=O)[C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(Cl)(=O)C(Cl)=O.C[ClH]N.[CH2:32]([N:34](CC)CC)C>C(Cl)Cl.CN(C=O)C>[CH3:32][NH:34][C:14]([C:4]1[C:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:2][N:7]=[N:6][C:5]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 69673498HCID 69673498, compound2×

Product 1

HCID 57330211HCID 57330211, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent4×

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 3,5-diphenylpyridazine-4-carboxylic acid (compound 6) (200 mg, 0.72 mmol) in CH2Cl2 (10 mL), oxalyl chloride (230 mg, 1.81 mmol), catalytical DMF were added and stirred at 0° C. for 1 h. After the complete consumption of the acid shown by TLC, the volatiles were removed under reduced pressure and the crude acid chloride obtained was taken up in dry CH2Cl2 (5 mL). A solution of methyl amino hydrochloride (238 mg, 3.62 mmol) in CH2Cl2 (5 mL) cooled to 0° C., triethylamine (219 mg, 2.17 mmol) and acid chloride were added dropwise at 5° C. After the completion of the starting material, the reaction mixture was diluted with CH2Cl2 (20 mL), washed with aq NaHCO3 (5 mL×1), brine (5 mL×1) and dried over anhydrous Na2SO4. The combined organic extracts were evaporated under reduced pressure to obtain the crude product which was purified by column chromatography (100-200 mesh silica gel, 30% EtOAc in hexane) to furnish N-methyl-3,5-diphenylpyridazine-4-carboxamide (compound 1) (100 mg, 47%) as a light orange solid.

Workup

  1. customAfter the complete consumption of the acid
  2. customthe volatiles were removed under reduced pressure
  3. customthe crude acid chloride obtained
  4. washwashed with aq NaHCO3 (5 mL×1), brine (5 mL×1)
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe combined organic extracts were evaporated under reduced pressure
  7. customto obtain the crude product which
  8. customwas purified by column chromatography (100-200 mesh silica gel, 30% EtOAc in hexane)

Sources & evidence

ORD record
ord-3ef9287d3400481d8ae34e7389b8fc3b
Source dataset
uspto-grants-2015_09
Patent number
US09145372B2

Reaction notes

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