Water → HCID 70232275, compound

HRID 1977431Notes

Reaction equation

HRID 1977431 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

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 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.

Workup

  1. temperatureat reflux for 48 hours
  2. filtrationsaturated NH4Cl and the resulting solid collected by filtration
  3. customThis material was purified by flash chromatography on silica gel eluting with 20% acetone-hexane
  4. customevaporated

Sources & evidence

ORD record
ord-55d7b56c8e164b2283fe89a5e22e4225
Source dataset
uspto-grants-2001_05
Patent number
US06232320B1

Reaction notes

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