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

HRID 2100479Notes

Reaction equation

HRID 2100479 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.[F:44][C:45]1[CH:50]=[CH:49][C:48]([F:51])=[CH:47][C:46]=1[CH2:52][CH2:53][O:54][CH2:55][C:56]([NH2:58])=[NH:57]>CN(C=O)C>[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH:58][C:56](=[NH:57])[CH2:55][O:54][CH2:53][CH2:52][C:46]1[CH:47]=[C:48]([F:51])[CH:49]=[CH:50][C:45]=1[F:44])=[O:6]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27360852,5-Dichloropyridine-3-carboxylic acidHCID 670990362-[2-(2,5-Difluoro-phenyl)-ethoxy]-acetamidine hydrochloride

Product 1

HCID 1405200772,5-dichloro-N-[2-[2-(2,5-difluorophenyl)ethoxy]ethanimidoyl]pyridine-3-carboxamideYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,5-Dichloronicotinic acid (50 mg, 260 μmol), TBTU (88 mg, 273 μmol) and DIPEA (130 μl, 781 μmol) were added to a solution of 2-[2-(2,5-difluoro-phenyl)-ethoxy]-acetamidine hydrochloride (65 mg, 260 μmol) in DMF (1 ml). The solution was stirred for 72 h at ambient temperature and poured onto ice water/dichloromethane 1/1. The layers were separated, the aqueous layer was extracted two times with dichloromethane, the combined extracts were washed with brine and dried over sodium sulfate. Removal of the solvent under reduced pressure yielded 2,5-dichloro-N-{2-[2-(2,5-difluoro-phenyl)-ethoxy]-1-imino-ethyl}-nicotinamide (97 mg, 250 μmol; 96%) as orange oil which was used in the next step without further purification. MS: m/e=388.2 [M+H+].

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted two times with dichloromethane
  3. washthe combined extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-4b8494a269964381bb0fee044b9f2c29
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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