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

HRID 2100553Notes

Reaction equation

HRID 2100553 reaction equation
[CH2:1]([C:5]1[CH:6]=[N:7][C:8]([Cl:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=O)[CH2:2][CH2:3][CH3:4].Cl.[Cl:16][C:17]1[CH:18]=[C:19]([CH2:23][CH2:24][O:25][CH2:26][C:27]([NH2:29])=[NH:28])[CH:20]=[CH:21][CH:22]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>>[CH2:1]([C:5]1[CH:6]=[N:7][C:8]([Cl:14])=[C:9]([CH:13]=1)[C:10]([NH:29][C:27](=[NH:28])[CH2:26][O:25][CH2:24][CH2:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([Cl:16])[CH:18]=1)=[O:12])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67098848HCID 67098848, compoundHCID 866166095-Butyl-2-chloro-nicotinic acid

Product 1

HCID 1405200715-butyl-2-chloro-N-[2-[2-(3-chlorophenyl)ethoxy]ethanimidoyl]pyridine-3-carboxamide

Procedure

In analogy to the procedure described in example 78.3, 5-butyl-2-chloro-nicotinic acid was reacted with 2-[2-(3-chloro-phenyl)-ethoxy]-acetamidine hydrochloride (example 79.2) in the presence of TBTU and DIPEA to give 5-butyl-2-chloro-N-{2-[2-(3-chloro-phenyl)-ethoxy]-1-imino-ethyl}-nicotinamide as yellow oil. MS: m/e=408.3 [M+H+].

Sources & evidence

ORD record
ord-9533b17234e943adb2a4b02b074b2b3a
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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