Triethylamine → HCID 66756744, compound

HRID 1915037Notes

Reaction equation

HRID 1915037 reaction equation
C[C:2]1[C:10]2[N:9]=[C:8]([C:11]([F:14])([F:13])[F:12])[N:7]([C:15]3[CH:20]=[N:19][C:18]([NH:21][C:22](=[O:31])[C:23]4[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=4[F:30])=[CH:17][N:16]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:32](O)=[O:33].C(Cl)(=O)C(Cl)=O.CCN(CC)CC.[CH2:48]([O:50][CH:51]([O:54][CH2:55][CH3:56])[CH2:52][NH2:53])[CH3:49]>C(Cl)Cl.CN(C=O)C>[CH2:48]([O:50][CH:51]([O:54][CH2:55][CH3:56])[CH2:52][NH:53][C:32]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:15]3[CH:20]=[N:19][C:18]([NH:21][C:22](=[O:31])[C:23]4[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=4[F:30])=[CH:17][N:16]=3)[C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][C:10]=2[CH:2]=1)=[O:33])[CH3:49]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 695242,2-DiethoxyethylamineHCID 66756847HCID 66756847, 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-b6d763e574b34d3394a23eca9603acdd
Source dataset
uspto-grants-2013_12
Patent number
US08614321B2

Reaction notes

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