Pyridine → HCID 178527479, compound

HRID 589674Notes

Reaction equation

HRID 589674 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:12][N:11]=[N:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:13][C:14]1[S:18][C:17]([S:19](Cl)(=[O:21])=[O:20])=[CH:16][CH:15]=1.N1C=CC=CC=1>C(Cl)Cl>[Br:13][C:14]1[S:18][C:17]([S:19]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[NH:12][N:11]=[N:10][N:9]=3)[CH:3]=2)(=[O:21])=[O:20])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27339245-Bromothiophene-2-sulfonyl chlorideHCID 178507542HCID 178507542, compound

Product 1

HCID 178527479HCID 178527479, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(3-aminophenyl)tetrazole (8.1 mg, 0.05 mmol), 5-bromothiophene-2-sulfonyl chloride (14 mg, 0.055 mmol) and pyridine (12 μL, 0.015 mmol) in CH2Cl2 (200 μL) was stirred at room temperature over night. The title compound was obtained after purification by preparative HPLC (16.7 mg, 43%). MS (ESI+) m/z 386 [M+H]+. The procedure was repeated on a larger scale with a modified purification method (flash chromatography, 10% MeOH in CH2Cl2), giving enough of the title compound to be used as starting material for further derivatisations.

Sources & evidence

ORD record
ord-1fa84993893140b8af4a7ac811e5dbff
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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