1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → methyl 4-(5-bromo-1-isopropyl-1H-benzo[d]imidazol-2-ylamino)benzoate

HRID 2273600Notes

Reaction equation

HRID 2273600 reaction equation
CN(C)CCCN=C=NCC.[Br:12][C:13]1[CH:14]=[C:15]([NH2:23])[C:16]([NH:19][CH:20]([CH3:22])[CH3:21])=[CH:17][CH:18]=1.[N:24]([C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=1)=[C:25]=S>O1CCCC1.C(OCC)(=O)C>[Br:12][C:13]1[CH:18]=[CH:17][C:16]2[N:19]([CH:20]([CH3:21])[CH3:22])[C:25]([NH:24][C:27]3[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=3)=[N:23][C:15]=2[CH:14]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 1380024-Methoxycarbonylphenyl isothiocyanateHCID 337851464-Bromo-1-N-isopropylbenzene-1,2-diamine

Product 1

HCID 67514052methyl 4-(5-bromo-1-isopropyl-1H-benzo[d]imidazol-2-ylamino)benzoateYield 71.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide (EDC, 331 mg, 2.18 mmol) is added to a solution of 4-bromo-N-1-isopropylbenzene-1,2-diamine (180 mg, 0.786 mmol) and methyl 4-isothiocyanatobenzoate (140 mg, 0.725 mmol) in tetrahydrofuran was added. The reaction was heated to reflux for 2 hr and cooled to room temperature. The mixture was diluted with ethyl acetate and washed with 1 N HCl and saturated sodium bicarbonate solution. The organic layer was concentrated and purified by Biotage column chromatography to give methyl 4-(5-bromo-1-isopropyl-1H-benzo[d]imidazol-2-ylamino)benzoate (202 mg)

Workup

  1. additionwas added
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 2 hr
  4. washwashed with 1 N HCl and saturated sodium bicarbonate solution
  5. concentrationThe organic layer was concentrated
  6. custompurified by Biotage column chromatography

Sources & evidence

ORD record
ord-c43c9456ce1f4a91a2cd323a5bc5d722
Source dataset
uspto-grants-2015_09
Patent number
US09125901B2

Reaction notes

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