Triethylamine → HCID 66756744, compound

HRID 2188816Notes

Reaction equation

HRID 2188816 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:3]=1[C:4]([NH:6][C:7]1[N:8]=[CH:9][C:10]([N:13]2[C:17]3[CH:18]=[CH:19][C:20]([C:22](O)=[O:23])=[CH:21][C:16]=3[N:15]=[C:14]2[C:25]([F:28])([F:27])[F:26])=[N:11][CH:12]=1)=[O:5].C(Cl)(=O)C(Cl)=O.CCN(CC)CC.[CH2:47]([O:49][CH:50]([O:53][CH2:54][CH3:55])[CH2:51][NH2:52])[CH3:48]>C(Cl)Cl.CN(C=O)C>[CH2:47]([O:49][CH:50]([O:53][CH2:54][CH3:55])[CH2:51][NH:52][C:22]([C:20]1[CH:19]=[CH:18][C:17]2[N:13]([C:10]3[CH:9]=[N:8][C:7]([NH:6][C:4](=[O:5])[C:3]4[C:29]([F:33])=[CH:30][CH:31]=[CH:32][C:2]=4[F:1])=[CH:12][N:11]=3)[C:14]([C:25]([F:28])([F:27])[F:26])=[N:15][C:16]=2[CH:21]=1)=[O:23])[CH3:48]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 695242,2-DiethoxyethylamineHCID 66756590HCID 66756590, compound

Product 1

HCID 66756744HCID 66756744, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a 50 mL roundbottom flask, was placed a solution of 1-(5-(2,6-difluorobenzamido)pyrazin-2-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazole-5-carboxylic acid (xiii) (50 mg, 0.11 mmol, 1.00 equiv) in DCM (15 ml) and DMF (1 drop). To the above stirred solution was added oxalyl dichloride (70 mg, 0.55 mmol, 5.00 equiv) dropwise at 0° C. The resulting solution was allowed to stir at 0° C. for 4 hours then was concentrated by evaporation under vacuum using a rotary evaporator. The residue was then taken up by DCM (10 ml) and then add dropwise to a stirred solution Of Et3N (40 mg, 3.00 equiv) and 2,2-diethoxyethanamine (15 mg, 0.11 mmol, 1.00 equiv) in DCM (10 mL) at 0° C. The resulting solution was allowed to stir overnight at room temperature, then was washed with H2O (2×100 mL) and dried over Na2SO4. Removal of the solvent and volatile components afforded the crude product 1-[5-(2,6-difluoro-benzoylamino)-pyrazin-2-yl]-2-trifluoromethyl-1H-benzoimidazole-5-carboxylic acid (2,2-diethoxy-ethyl)-amide (xiv) (50 mg, 64% yield) as a yellow solid that was used directly in the next step.

Workup

  1. customInto a 50 mL roundbottom flask, was placed
  2. concentrationthen was concentrated by evaporation under vacuum
  3. customa rotary evaporator
  4. stirringto stir overnight at room temperature
  5. washwas washed with H2O (2×100 mL)
  6. dry with materialdried over Na2SO4
  7. customRemoval of the solvent and volatile components

Sources & evidence

ORD record
ord-468eb840cec74960a7537a58db495683
Source dataset
uspto-grants-2012_12
Patent number
US08324219B2

Reaction notes

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