Triethylamine → HCID 178521525, compound

HRID 900726Notes

Reaction equation

HRID 900726 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:8]=[C:9]([SH:12])[NH:10][N:11]=2)[CH:2]=1.C(N(CC)CC)C.Cl[CH2:21][C:22]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=1)=[O:23]>CN(C=O)C>[Cl:31][C:27]1[CH:26]=[C:25]([NH:24][C:22](=[O:23])[CH2:21][S:12][C:9]2[NH:10][N:11]=[C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[N:8]=2)[CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 137639Acetanilide, 2,3'-dichloro-HCID 178527843HCID 178527843, compound

Product 1

HCID 178521525HCID 178521525, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The thiol intermediate prepared in Step B (101 mg, 0.567 mmol) was dissolved in DMF (2 ml) and triethylamine (0.24 ml, 1.7 mmol). 2,3′-dichloroacetanilide (116 mg, 0.567 mmol) was added and allowed to stir at room temperature overnight. The mixture was loaded directly onto an HPLC reverse phase column and purified by water to acetonitrile gradient in the presence of 0.1% trifluoroacetic acid. The aqueous phase was evaporated by lyophilization to yield the title compound as a fluffy white solid (166 mg, 85% yield). MS (ES) 346.5 (M+H)+

Workup

  1. custompurified by water to acetonitrile gradient in the presence of 0.1% trifluoroacetic acid
  2. customThe aqueous phase was evaporated by lyophilization

Sources & evidence

ORD record
ord-b2f5092f3d04423a81a5a2d0ae277712
Source dataset
uspto-grants-2008_04
Patent number
US07361669B2

Reaction notes

Loading…