Diisopropylethylamine → 3-chloro-N-[2-(2-naphthalen-2-ylethoxy)ethanimidoyl]pyrazine-2-carboxamide

HRID 2076831Notes

Reaction equation

HRID 2076831 reaction equation
[Cl:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][N:7]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.Cl.[CH:43]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:46]=[CH:45][C:44]=1[CH2:53][CH2:54][O:55][CH2:56][C:57]([NH2:59])=[NH:58]>CN(C=O)C.ClCCl>[NH:58]=[C:57]([NH:59][C:8]([C:3]1[C:2]([Cl:1])=[N:7][CH:6]=[CH:5][N:4]=1)=[O:10])[CH2:56][O:55][CH2:54][CH2:53][C:44]1[CH:45]=[CH:46][C:47]2[C:52](=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:43]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 15019003-Chloro-2-pyrazine-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67099300HCID 67099300, compound

Product 1

HCID 1527662053-chloro-N-[2-(2-naphthalen-2-ylethoxy)ethanimidoyl]pyrazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of nitrogen, 3-chloro-2-pyrazinecarboxylic acid (Tyger, 250 mg), TBTU (532 mg), and diisopropylethylamine (1.34 ml) were added to a solution of 2-(2-naphthalen-2-yl-ethoxy)-acetamidine hydrochloride (417 mg) in DMF (5 ml). The reaction mixture was stirred for 2 h at r.t., diluted with dichloromethane and washed with water. The organic layer was dried (Na2SO4), filtered, and the solvent was evaporated. The obtained, crude title compound (567 mg) was used without further purification in the next step.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe obtained, crude title compound (567 mg) was used without further purification in the next step

Sources & evidence

ORD record
ord-efa7859ecccb4c28ac87a2c733e58662
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Reaction notes

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