Water → HCID 70232275, compound

Reaction equation

[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][C:9]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[S:4][C:3]=1[C:19]([NH2:21])=[O:20].C(N(CC)CC)C.O.[O:30]1CCC[CH2:31]1>>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([O:11][C:9]2[C:10]3[C:2]4[NH:1][C:31](=[O:30])[NH:21][C:19](=[O:20])[C:3]=4[S:4][C:5]=3[CH:6]=[N:7][CH:8]=2)=[CH:17][CH:16]=1

Participants

Reactant 4

HCID 962Water

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 9923070HCID 9923070, compound

Product 1

HCID 70232275HCID 70232275, compoundYield 51%

Procedure

To a suspension of Example 131D (70 mg, 0.22 mmol) in anhydrous tetrahydrofuran (5 mL) under nitrogen atmosphere was added 1,1-carbonyldiimidazole (71 mg, 0.44 mmol) and triethylamine (60 μL, 0.44 mmol). The reaction mixture was stirred at reflux for 48 hours and then ambient temperature for an additional 24 hours. The reaction mixture was poured into a 1:1 solution of water: saturated NH4Cl and the resulting solid collected by filtration. This material was purified by flash chromatography on silica gel eluting with 20% acetone-hexane. The desired fractions were combined, evaporated and slurried in hot EtOAC to obtain title compound (39 mg) in 51% yield.