Pyridine → HCID 178461801, compound

HRID 1455004Notes

Reaction equation

HRID 1455004 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][S:6][C:7]1[N:12]=[C:11]([OH:13])[CH:10]=[C:9]([NH:14][C@H:15]([CH3:18])[CH2:16][OH:17])[N:8]=1.N1C=CC=CC=1.[S:28]1[CH:32]=[N:31][N:30]=[C:29]1[SH:33].BrBr>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][S:6][C:7]2[N:12]=[C:11]([OH:13])[C:10]([S:33][C:29]3[S:28][CH:32]=[N:31][N:30]=3)=[C:9]([NH:14][C@H:15]([CH3:18])[CH2:16][OH:17])[N:8]=2)[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24408BromineHCID 178461795HCID 178461795, compoundHCID 178527973HCID 178527973, compound

Product 1

HCID 178461801HCID 178461801, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of Example 3 (0.12 g), pyridine (50 μl) and 1,3,4-thiadiazole-2-thiol (0.18 g) were dissolved in DMF (3 ml) and bromine (18 μl) added dropwise. The reaction mixture was stirred for 1 h before being purified directly by reverse phase HPLC (95-75% 0.02M ammonium hydroxide/acetonitrile) to yield the title product as a white solid. Yield 0.15 g.

Workup

  1. custombefore being purified directly by reverse phase HPLC (95-75% 0.02M ammonium hydroxide/acetonitrile)

Sources & evidence

ORD record
ord-fd8ddb8f3ba94915a7e835af318486dd
Source dataset
uspto-grants-2009_01
Patent number
US07482355B2

Reaction notes

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