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

HRID 2100543Notes

Reaction equation

HRID 2100543 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.[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[CH2:23][CH2:24][O:25][CH2:26][C:27]([NH2:29])=[NH:28].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:29][C:27](=[NH:28])[CH2:26][O:25][CH2:24][CH2:23][C:14]1[CH:15]=[CH:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=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 67099300HCID 67099300, compound

Product 1

HCID 1405200682,5-dichloro-N-[2-(2-naphthalen-2-ylethoxy)ethanimidoyl]pyridine-3-carboxamide

Procedure

In analogy to the procedure described in example 78.3, 2,5-dichloronicotinic acid was reacted with 2-(2-naphthalen-2-yl-ethoxy)-acetamidine hydrochloride in the presence of TBTU and DIPEA to give 2,5-dichloro-N-[1-imino-2-(2-naphthalen-2-yl-ethoxy)-ethyl]-nicotinamide as yellow oil. MS: m/e=402.3 [M+H+].

Sources & evidence

ORD record
ord-c7c5a3431ec74e3d87a68226ee3ca525
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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