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

HRID 2100555Notes

Reaction equation

HRID 2100555 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.[F:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[CH2:24][CH2:25][O:26][CH2:27][C:28]([NH2:30])=[NH:29].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:30][C:28](=[NH:29])[CH2:27][O:26][CH2:25][CH2:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[F:16])=[O:12])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 670990362-[2-(2,5-Difluoro-phenyl)-ethoxy]-acetamidine hydrochlorideHCID 866166095-Butyl-2-chloro-nicotinic acid

Product 1

HCID 1405200665-butyl-2-chloro-N-[2-[2-(2,5-difluorophenyl)ethoxy]ethanimidoyl]pyridine-3-carboxamide

Procedure

In analogy to the procedure described in example 78.3, 5-butyl-2-chloro-nicotinic acid (example 126.3) was reacted with 2-[2-(2,5-difluoro-phenyl)-ethoxy]-acetamidine hydrochloride (example 78.2) in the presence of TBTU and DIPEA to give 5-butyl-2-chloro-N-{2-[2-(2,5-difluoro-phenyl)-ethoxy]-1-imino-ethyl}-nicotinamide as orange oil. MS: m/e=410.1 [M+H+].

Sources & evidence

ORD record
ord-e37acd02a3db4a3892e1fb356be06cdc
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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