Hydrochloric Acid → HCID 178521913, compound

HRID 1360983Notes

Reaction equation

HRID 1360983 reaction equation
[N:1]1[C:5]2=[CH:6][CH:7]=[C:8]([C:10]([OH:12])=O)[CH2:9][C:4]2=[N:3][N:2]=1.C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.Cl>CN(C=O)C.C(OCC)(=O)C>[C:35]1([NH:34][C:10]([C:8]2[CH:7]=[CH:6][C:5]3[NH:1][N:2]=[N:3][C:4]=3[CH:9]=2)=[O:12])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 534427314H-Benzo[d][1,2,3]triazole-5-carboxylic acid

Product 1

HCID 178521913HCID 178521913, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzotriazole-5-carboxylic acid (856 mg), HOAt (715 mg) and EDAC (1.00 g) were dissolved in DMF (17.5 mL) and the mixture was stirred at room temperature 1 hour. A 0.5 mL aliquot of this mixture was added to aniline (13.7 μL, 0.15 mmol) and the resulting mixture was vigorously shaken at room temperature for 16 hours. 1N hydrochloric acid (2 mL) and ethyl acetate (1 mL) were added and the mixture was vigorously shaken at room temperature for 2 hours. The organic phase was isolated and concentrated in vacuo to afford the title compound.

Workup

  1. stirringthe resulting mixture was vigorously shaken at room temperature for 16 hours
  2. stirringthe mixture was vigorously shaken at room temperature for 2 hours
  3. customThe organic phase was isolated
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-70a5426c3e1a44c7accb8bcccb74297a
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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