Tetrahydrofuran → HCID 824395, compound
Reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.CCN(C(C)C)C(C)C.CN(C(O[N:28]1[N:36]=N[C:30]2C=CC=C[C:29]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C[O:45]CC1>>[C:29]([NH:28][NH:36][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=1)(=[O:45])[CH3:30]Participants
5
Procedure
To a suspension of 3-iodobenzoic acid (2.0 g, 8.06 mmol) in 60 ml of THF there are added, in succession, DIPEA (1.83 ml, 10.48 mmol) and TBTU (2.59 g, 8.06 mmol). The reaction mixture is stirred overnight at ambient temperature. 1.19 g (16.12 mmol) of acetyl hydrazide are added and the reaction mixture is heated at reflux for 30 hours. After evaporation to dryness, the residue is taken up in water with a small amount of CH2Cl2; a thick precipitate forms, which is filtered off to yield the expected product.