1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(3,5-Dichloro-pyridin-4-yl-amino)-1-methyl-1H-benzimidazole-5-carboxylic acid methyl ester

HRID 578054Notes

Reaction equation

HRID 578054 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH3:11])=[C:6]([NH2:12])[CH:5]=1.[Cl:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([Cl:24])[C:20]=1[N:21]=[C:22]=S.C(N=C=NCCCN(C)C)C>C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH3:11])[C:22]([NH:21][C:20]3[C:15]([Cl:14])=[CH:16][N:17]=[CH:18][C:19]=3[Cl:24])=[N:12][C:6]=2[CH:5]=1)=[O:13]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15586064Methyl 3-amino-4-(methylamino)benzoateHCID 59646493HCID 59646493, compound

Product 1

HCID 672335772-(3,5-Dichloro-pyridin-4-yl-amino)-1-methyl-1H-benzimidazole-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-amino-4-methylamino-benzoic acid methyl ester (360 mg, 2.0 mmol) and 3,5-dichloro-4-isothiocyanato-pyridine (585 mg, 70%, 2.0 mmol) in 10 mL ethyl acetate was stirred for 2 h at ambient temperature. 1-Ethyl-3-(3′-dimethylaminopropyl)-carbodiimide*HCl (383 mg, 2.0 mmol) was added and the mixture stirred overnight. The mixture was concentrated i. vac., the residue was taken up in DMF and purified by RP-HPLC.

Workup

  1. stirringthe mixture stirred overnight
  2. concentrationThe mixture was concentrated i
  3. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-9939ebbe41a648e78607b8c353f4272d
Source dataset
uspto-grants-2015_05
Patent number
US09040565B2

Reaction notes

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