Diisopropylethylamine → 3-chloro-N-[2-[2-(2,5-difluorophenyl)ethoxy]ethanimidoyl]pyrazine-2-carboxamide

HRID 2076813Notes

Reaction equation

HRID 2076813 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[CH2:10][CH2:11][O:12][CH2:13][C:14]([NH2:16])=[NH:15].[Cl:17][C:18]1[C:19]([C:24](O)=[O:25])=[N:20][CH:21]=[CH:22][N:23]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[F:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[CH2:10][CH2:11][O:12][CH2:13][C:14]([NH:16][C:24]([C:19]1[C:18]([Cl:17])=[N:23][CH:22]=[CH:21][N:20]=1)=[O:25])=[NH:15]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 15019003-Chloro-2-pyrazine-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 670990362-[2-(2,5-Difluoro-phenyl)-ethoxy]-acetamidine hydrochloride

Product 1

HCID 1412152603-chloro-N-[2-[2-(2,5-difluorophenyl)ethoxy]ethanimidoyl]pyrazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-[2-(2,5-Difluoro-phenyl)-ethoxy]-acetamidine hydrochloride (158 mg, 0.631 mmol) was dissolved in DMF (3 ml) and 3-chloro-2-pyrazine-carboxylic acid (100 mg, 0.631 mmol), TBTU (213 mg, 0.662 mmol) and DIPEA (565 μl, 3.15 mmol) were added. The reaction mixture was stirred at ambient temperature for 4.5 h. Then water was added and the mixture was extracted three times with CH2Cl2. The combined organic extracts were washed with water and brine, dried (Na2SO4) and evaporated. The crude title compound (195 mg, brown gum) was used for the next reaction step without further purification. MS: m/e=355.2 [M+H+].

Workup

  1. extractionthe mixture was extracted three times with CH2Cl2
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe crude title compound (195 mg, brown gum) was used for the next reaction step without further purification

Sources & evidence

ORD record
ord-9cd65c342cfd48b5ad6b7a84e8fda054
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Reaction notes

Loading…