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

HRID 2100548Notes

Reaction equation

HRID 2100548 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]([CH2:21][CH2:22][O:23][CH2:24][C:25]([NH2:27])=[NH:26])[CH:18]=[CH:19][CH:20]=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]([CH2:11][CH3:12])=[CH:7][C:3]=1[C:4]([NH:27][C:25](=[NH:26])[CH2:24][O:23][CH2:22][CH2:21][C:17]1[CH:18]=[CH:19][CH:20]=[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 67098848HCID 67098848, compound

Product 1

HCID 1405200672-chloro-N-[2-[2-(3-chlorophenyl)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-phenyl)-ethoxy]-acetamidine hydrochloride (example 79.2) in the presence of TBTU and DIPEA to give 2-chloro-N-{2-[2-(3-chloro-phenyl)-ethoxy]-1-imino-ethyl}-5-ethyl-nicotinamide as yellow oil. MS: m/e=380.2 [M+H+].

Sources & evidence

ORD record
ord-10e87c1c17ef4e04b5222571e11a2c5d
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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