Dimethylformamide → HCID 71532041, compound

HRID 1505761Notes

Reaction equation

HRID 1505761 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([NH:11]N1C2C=CC=C(C(O)=O)C=2N=C1)=[O:10].Cl.[CH2:27]([C:29]([NH:31][CH2:32][CH2:33][CH2:34][N:35]([CH3:37])C)=N)[CH3:28].O[N:39]1[C:43]2C=C[CH:46]=[CH:47][C:42]=2N=N1.[F:48][C:49]([F:59])([F:58])[C:50]1[CH:57]=[CH:56][CH:55]=CC=1CN.CN(C=[O:64])C>C(N(CC)CC)C>[F:59][C:49]([F:48])([F:58])[C:50]1[CH:57]=[CH:56][CH:55]=[CH:28][C:27]=1[CH2:29][NH:31][C:32]([C:33]1[C:34]2[N:35]=[CH:37][NH:39][C:43]=2[CH:42]=[C:47]([NH:11][C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:1])([F:24])[F:25])=[O:10])[CH:46]=1)=[O:64]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 764472-(Trifluoromethyl)benzylamineHCID 131734355HCID 131734355, compoundHCID 178458058HCID 178458058, compound

Product 1

HCID 71532041HCID 71532041, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 6-({[2-(trifluoromethyl)phenyl]carbonyl}amino-1H-benzimidazole-4-carboxylic acid (50 mg) in DMF (2 mL) were added N′-(ethylcarbonimidoyl)-N,N-dimethyl-1,3-propanediamine hydrochloride (33 mg), 1-hydroxybenzotriazol (23 mg) and triethylamine (24 μL), and 2-(trifluoromethyl)benzylamine (24 μL) was added under ice-cooling, and the solution was stirred at room temperature overnight. The mixture was poured into ice water and extracted with ethyl acetate. The ethyl acetate layer was washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was washed with n-hexane/ethyl acetate (1:1), and collected by filtration to obtain the titled compound (61 mg) as colorless powder. MS (ESI+) m/z 507 (M+H)+

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed sequentially with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. washThe residue was washed with n-hexane/ethyl acetate (1:1)
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-08b114ce0916467a9baba1267135eb5e
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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