Pyridine → HCID 42629394, compound

HRID 1696736Notes

Reaction equation

HRID 1696736 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:11](Cl)(=[O:13])=[O:12])[S:5][C:6]=1[CH2:7][CH2:8][O:9][CH3:10].[O:15]([C:17]#[N:18])[Na].N1C=CC=CC=1.[Br:25][C:26]1[CH:31]=[C:30]([NH2:32])[N:29]=[C:28]([NH2:33])[CH:27]=1>C(#N)C>[NH2:33][C:28]1[N:29]=[C:30]([NH:32][C:17]([NH:18][S:11]([C:4]2[S:5][C:6]([CH2:7][CH2:8][O:9][CH3:10])=[C:2]([Cl:1])[CH:3]=2)(=[O:13])=[O:12])=[O:15])[CH:31]=[C:26]([Br:25])[CH:27]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 114353934-Bromo-2,6-diaminopyridineHCID 86616721HCID 86616721, compoundHCID 178418852HCID 178418852, compound

Product 1

HCID 42629394HCID 42629394, compoundYield 16.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

4-Chloro-5-(2-methoxy-ethyl)-thiophene-2-sulfonyl chloride (73 mg) was dissolved in acetonitrile (1.5 mL), NaOCN (38 mg) and pyridine (130 mL) was added to the solution. The mixture was stirred for 4 h at 25° C. After that 4-bromo-pyridine-2,6-diamine (50 mg) was added to the mixture as solid. The resulting yellow suspension was stirred for 2 h at 25° C. The suspension was evaporated to dryness, dissolved in DMSO (1.5 mL) and purified with preparative HPLC. N-[(6-amino-4-bromopyridin-2-yl)carbamoyl]-4-chloro-5-(2-methoxyethyl)-thiophene-2-sulfonamide (21 mg, 16.8% yield) was obtained as amorphous white solid.

Workup

  1. stirringThe resulting yellow suspension was stirred for 2 h at 25° C
  2. customThe suspension was evaporated to dryness
  3. dissolutiondissolved in DMSO (1.5 mL)
  4. custompurified with preparative HPLC

Sources & evidence

ORD record
ord-c33149b2defb40d18aae61ea5479af84
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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