1-Hydroxybenzotriazole → 5-(2-(5-(3,4-Dichlorophenyl)furan-2-yl)ethylcarbamoyl)pyrazine-2-carboxylic acid

HRID 872441Notes

Reaction equation

HRID 872441 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([OH:9])=O)[N:4]=[CH:3][C:2]=1[C:10]([OH:12])=[O:11].C1C=CC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC.Cl.[Cl:36][C:37]1[CH:38]=[C:39]([C:44]2[O:48][C:47]([CH2:49][CH2:50][NH2:51])=[CH:46][CH:45]=2)[CH:40]=[CH:41][C:42]=1[Cl:43].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:36][C:37]1[CH:38]=[C:39]([C:44]2[O:48][C:47]([CH2:49][CH2:50][NH:51][C:7]([C:5]3[N:4]=[CH:3][C:2]([C:10]([OH:12])=[O:11])=[N:1][CH:6]=3)=[O:9])=[CH:46][CH:45]=2)[CH:40]=[CH:41][C:42]=1[Cl:43]

Participants

7

Reactant 5

HCID 757711-Hydroxybenzotriazole2×HCID 81531Diisopropylethylamine3×HCID 255280Pyrazine-2,5-dicarboxylic acid2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 671683442-(5-(3,4-Dichlorophenyl)furan-2-yl)ethanamine hydrochloride

Product 1

HCID 671689775-(2-(5-(3,4-Dichlorophenyl)furan-2-yl)ethylcarbamoyl)pyrazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Pyrazine-2,5-dicarboxylic acid (0.58 g; 3.42 mmol), anhydrous HOBt (0.69 g; 5.13 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.98 g: 5.13 mmol) were added to 5 ml of DCM. 2-(5-(3,4-dichlorophenyl)furan-2-yl)-ethanamine hydrochloride (1.0 g; 3.42 mmol) and DIPEA (0.89 ml; 5.13 mmol) were dissolved in 5 ml of DCM and added dropwise to the previous mixture. The reaction mixture was stirred overnight after which pyrazine-2,5-dicarboxylic acid (0.58 g; 1.59 mmol) and DIPEA (0.60 ml; 3.42 mmol) were added and the mixture was again stirred for 5 h. Anhydrous HOBt (0.69 g; 5.13 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.98 g: 5.13 mmol) and DIPEA (0.89 ml; 5.13 mmol) were again added to drive the reaction to completion. After overnight stirring the mixture was diluted with 20 ml of DCM and washed with 3×10 ml water. The organic phase was dried over Na2SO4, filtered and used as such without further purification.

Workup

  1. additionadded dropwise to the previous mixture
  2. additionwere added
  3. customthe reaction to completion
  4. stirringAfter overnight stirring the mixture
  5. washwashed with 3×10 ml water
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. customsuch without further purification

Sources & evidence

ORD record
ord-0ac02fbbf8cb4d67a2837207a060e9e0
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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