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

HRID 2100482Notes

Reaction equation

HRID 2100482 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]([CH2:20][CH2:21][O:22][CH2:23][C:24]([NH2:26])=[NH:25])[CH:17]=[CH:18][CH:19]=1.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:26][C:24](=[NH:25])[CH2:23][O:22][CH2:21][CH2:20][C:16]1[CH:17]=[CH:18][CH:19]=[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 67098848HCID 67098848, compound

Product 1

HCID 1405200762,5-dichloro-N-[2-[2-(3-chlorophenyl)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-phenyl)-ethoxy]-acetamidine hydrochloride in the presence of TBTU and DIPEA to give 2,5-dichloro-N-{2-[2-(3-chloro-phenyl)-ethoxy]-1-imino-ethyl}-nicotinamide as orange oil. MS: m/e=388.1 [M+H+].

Sources & evidence

ORD record
ord-387338be66e34e879ebdc713da0eefa8
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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