Diisopropylethylamine → 2,5-dichloro-N-[2-[2-(3-chloro-4-fluorophenyl)ethoxy]ethanimidoyl]pyridine-3-carboxamide

HRID 2100491Notes

Reaction equation

HRID 2100491 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.Cl.[Cl:13][C:14]1[CH:15]=[C:16]([CH2:21][CH2:22][O:23][CH2:24][C:25]([NH2:27])=[NH:26])[CH:17]=[CH:18][C:19]=1[F:20].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>>[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH:27][C:25](=[NH:26])[CH2:24][O:23][CH2:22][CH2:21][C:16]1[CH:17]=[CH:18][C:19]([F:20])=[C:14]([Cl:13])[CH:15]=1)=[O:6]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27360852,5-Dichloropyridine-3-carboxylic acidHCID 670983972-[2-(3-Chloro-4-fluoro-phenyl)-ethoxy]-acetamidine hydrochloride

Product 1

HCID 1405200702,5-dichloro-N-[2-[2-(3-chloro-4-fluorophenyl)ethoxy]ethanimidoyl]pyridine-3-carboxamide

Procedure

In analogy to the procedure described in example 78.3, 2,5-dichloronicotinic acid was reacted with 2-[2-(3-chloro-4-fluoro-phenyl)-ethoxy]-acetamidine hydrochloride in the presence of TBTU and DIPEA to give 2,5-dichloro-N-{2-[2-(3-chloro-4-fluoro-phenyl)-ethoxy]-1-imino-ethyl}-nicotinamide as orange oil. MS: m/e=404.2 [M+H+].

Sources & evidence

ORD record
ord-ed5596dbcdf547a0b09b422da044bfc2
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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