287730-14-7|5,6-Dichloro-1H-benzimidazole-2-carboxylic acid| Ambeed

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Quality Control of [ 287730-14-7 ] Purity: 95% SDS Specification

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Product Details of [ 287730-14-7 ]

CAS No. :	287730-14-7
Formula :	C₈H₄Cl₂N₂O₂
M.W :	231.04
SMILES Code :	O=C(C1=NC2=CC(Cl)=C(Cl)C=C2N1)O
MDL No. :	MFCD20265549
InChI Key :	PZVBZTDCNFRTLA-UHFFFAOYSA-N
Pubchem ID :	10036861

Safety of [ 287730-14-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340

Application In Synthesis of [ 287730-14-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 287730-14-7 ]

[ 287730-14-7 ] Synthesis Path-Downstream 1~26

1
[ 3584-64-3 ]
[ 287730-14-7 ]

References: [1]Archiv der Pharmazie,2000,vol. 333,p. 123 - 129.
[2]Indian Journal of Heterocyclic Chemistry,2014,vol. 24,p. 87 - 92.

2
[ 5348-42-5 ]
[ 287730-14-7 ]

References: [1]Archiv der Pharmazie,2000,vol. 333,p. 123 - 129.
[2]Indian Journal of Heterocyclic Chemistry,2014,vol. 24,p. 87 - 92.
[3]Journal of Medicinal Chemistry,2020,vol. 63,p. 205 - 215.

4
[ 102877-78-1 ]
[ 287730-14-7 ]
N-[4-(pyridine-4-yloxy)phenyl]-5,6-dichloro-1H-benzimidazole-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃;	0.064 MMOL of BENZIMIDAZOLECARBOXYLIC acid 4j was suspended in DMF together with 0.064 MMOL of the amine 5a, a solution of TBTU (0.096 MMOL) in DMF, HOBT (0.026 MMOL) in DMF and 0. 32 mmol of DIPEA were added successively, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with water, and the resulting precipitate was filtered off with suction and washed with water. Yield: 51%, pale-brown solid

References: [1]Patent: WO2005/4863,2005,A1 .Location in patent: Page/Page column 140.

5
[ 80650-45-9 ]
[ 287730-14-7 ]
N-[4-(pyridine-3-yloxy)phenyl]-5,6-dichloro-1H-benzimidazole-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20.0℃;	0.064 mmol of benzimidazolecarboxylic acid 4j was suspended in DMF together with 0.064 mmol of the amine 5b, a solution of TBTU (0.096 MMOL) in DMF, HOBT (0.026 MMOL) in DMF and 0.32 mmol of DIPEA were added successively, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with water, and the resulting precipitate was filtered off with suction and washed with water. Yield : 46%, pale-brown solid

References: [1]Patent: WO2005/4863,2005,A1 .Location in patent: Page/Page column 145.

6
[ 27692-74-6 ]
[ 287730-14-7 ]
N-[4-(pyridine-4-ylmethyl)phenyl]-5,6-dichloro-1H-benzimidazole-2-carboxylic acid amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20.0℃;	0.064 mmol BENZIMIDAZOLE carboxylic acid 4J and 0.064 mmol amine 5E are suspended together in DMF, treated consecutively with a solution of TBTU (0.096 MMOL) in DMF, a solution of HOBT (0. 026 MMOL) in DMF and 0. 32 MMOL DIPEA, and stirred at room temperature overnight. The reaction mixture is diluted with water, the formed precipitate is removed by filtration by suction and dried. Yield : 26 %, beige solid

References: [1]Patent: WO2005/4863,2005,A1 .Location in patent: Page/Page column 159.

7
[ 5680-79-5 ]
[ 287730-14-7 ]
[ 1266326-81-1 ]

References: [1]ACS Medicinal Chemistry Letters,2010,vol. 1,p. 526 - 529.

8
[ 287730-14-7 ]
C₁₀H₇Cl₂N₃O₃ [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2010,vol. 1,p. 526 - 529.

9
[ 110-89-4 ]
[ 287730-14-7 ]
[ 1352002-33-5 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: N,N’-Carbonyldiimidazole (0.405g, 2.5 mmol) was added, under stirring in a nitrogen atmosphere, to a solution of the 5-chloro benzimidazolecarboxylic acid IVc (2.5 mmol) in 4 ml of anhydrous DMF. After carbon dioxide evolution had ceased, a solution of the N methylpiperazine (2.5 mmol) in 2 ml of anhydrous DMF was added to the reaction mixture, which was concentrated to dryness and the crude product was purified by column chromatography and then recrystallized to get Va as colourless solid, MP (274-2760). Compounds Vb-i were prepared adopting similar procedure from IVa and IVb and appropriate amines (N-ethyl piperazine, piperidine). The structures of the compounds IVa-i were confirmed based on their analytical and spectral data and analytical data as shown in Table-2.

References: [1]Journal of Heterocyclic Chemistry,2011,vol. 48,p. 1317 - 1322.
[2]Indian Journal of Heterocyclic Chemistry,2014,vol. 24,p. 87 - 92.

10
[ 109-01-3 ]
[ 287730-14-7 ]
[ 673487-17-7 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: N,N’-Carbonyldiimidazole (0.405g, 2.5 mmol) was added, under stirring in a nitrogen atmosphere, to a solution of the 5-chloro benzimidazolecarboxylic acid IVc (2.5 mmol) in 4 ml of anhydrous DMF. After carbon dioxide evolution had ceased, a solution of the N methylpiperazine (2.5 mmol) in 2 ml of anhydrous DMF was added to the reaction mixture, which was concentrated to dryness and the crude product was purified by column chromatography and then recrystallized to get Va as colourless solid, MP (274-2760). Compounds Vb-i were prepared adopting similar procedure from IVa and IVb and appropriate amines (N-ethyl piperazine, piperidine). The structures of the compounds IVa-i were confirmed based on their analytical and spectral data and analytical data as shown in Table-2.

References: [1]Journal of Heterocyclic Chemistry,2011,vol. 48,p. 1317 - 1322.
[2]Indian Journal of Heterocyclic Chemistry,2014,vol. 24,p. 87 - 92.

11
[ 4319-49-7 ]
[ 287730-14-7 ]
[ 1352002-43-7 ]