1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-Methyl-nicotinic acid N'-[2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carbonyl]-hydrazide

HRID 1360719Notes

Reaction equation

HRID 1360719 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]([NH:20][NH2:21])=[O:19])[CH:15]=[CH:14][C:12]=2[N:13]=1.[CH3:22][C:23]1[CH:24]=[N:25][CH:26]=[C:27]([CH:31]=1)[C:28](O)=[O:29].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CCOC(C)=O.O.CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]([NH:20][NH:21][C:28](=[O:29])[C:27]3[CH:31]=[C:23]([CH3:22])[CH:24]=[N:25][CH:26]=3)=[O:19])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2562085-Methylnicotinic acidHCID 577865852-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide2×

Product 1

HCID 669667675-Methyl-nicotinic acid N'-[2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carbonyl]-hydrazideYield 61.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a yellow solution of 0.200 g (0.623 mmol) of 2-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide (Intermediate 1), 0.0854 g (0.623 mmol) of 5-methyl nicotinic acid, and 5 mL of DMF was added 0.1453 g (0.747 mmol) of EDCI, and 0.1010 g (0.747 mmol) of HOBt. Allowed to stir at r.t. for 18 h. Added 5 mL of water, EtOAc and filtered off solid, to give 0.1680 g of the title compound. Used directly in next reaction. MS (m/z) 440.0 M (+1), tR=1.00, Meth 10

Workup

  1. filtrationfiltered off solid

Sources & evidence

ORD record
ord-725f3a2f45c7403881616c09a57b2392
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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