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

HRID 2100557Notes

Reaction equation

HRID 2100557 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([CH2:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[Cl:14][C:15]1[CH:16]=[C:17]([CH2:22][CH2:23][O:24][CH2:25][C:26]([NH2:28])=[NH:27])[CH:18]=[CH:19][C:20]=1[F:21].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]([CH2:11][CH3:12])=[CH:7][C:3]=1[C:4]([NH:28][C:26](=[NH:27])[CH2:25][O:24][CH2:23][CH2:22][C:17]1[CH:18]=[CH:19][C:20]([F:21])=[C:15]([Cl:14])[CH:16]=1)=[O:6]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 200786802-Chloro-5-ethyl-nicotinic acidHCID 670983972-[2-(3-Chloro-4-fluoro-phenyl)-ethoxy]-acetamidine hydrochloride

Product 1

HCID 1405200642-chloro-N-[2-[2-(3-chloro-4-fluorophenyl)ethoxy]ethanimidoyl]-5-ethylpyridine-3-carboxamide

Procedure

In analogy to the procedure described in example 78.3, 2-chloro-5-ethyl-nicotinic acid (example 124.1) was reacted with 2-[2-(3-chloro-4-fluoro-phenyl)-ethoxy]-acetamidine hydrochloride (example 82.2) in the presence of TBTU and DIPEA to give 2-chloro-N-{2-[2-(3-chloro-4-fluoro-phenyl)-ethoxy]-1-imino-ethyl}-5-ethyl-nicotinamide as yellow oil. MS: m/e=398.1 [M+H+].

Sources & evidence

ORD record
ord-c85a028ebe7442e09fcbc85ab3dacd4a
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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