HCID 86602012, compound → HCID 17981866, compound

HRID 2252066Notes

Reaction equation

HRID 2252066 reaction equation
[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16]3[N:17]=[C:18]([CH:35]=[O:36])[N:19](COCC[Si](C)(C)C)[C:20]=3[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:37])(=[O:6])=[O:5])([CH3:3])[CH3:2]>C(O)C.O>[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16]3[N:17]=[C:18]([CH:35]=[O:36])[NH:19][C:20]=3[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:37])(=[O:5])=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86602012HCID 86602012, compound

Product 1

HCID 17981866HCID 17981866, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Add to a solution of 1-isopropylsulfonyl-2-amino-6-(1-(trimethylsilylethoxymethyl)-2-(formyl)-5-(phenyl)-imidazolyl)-benzimidazole (100 mg, 0.185 mmol) in ethanol (4 mL) HCl (37%, 4 mL) and stir at room temperature for 4 hours. Dilute the mixture with water (20 mL) and wash with EtOAc (3×10 mL). Add to the aqueous phase NaOH (15%) until pH=6-7 and extract the mixture with EtOAc (3×20 mL). Dry (MgSO4) the combined organic layers and concentrate in vacuo. Purify the residue in solid phase extraction (SPE) cartridge (Oasis™) and then by HPLC to obtain a white solid, 8 mg, 10% yield. MS(ES+): m/z=410 (M+H)+

Workup

  1. washwash with EtOAc (3×10 mL)
  2. additionAdd to the aqueous phase NaOH (15%) until pH=6-7
  3. extractionextract the mixture with EtOAc (3×20 mL)
  4. dry with materialDry (MgSO4) the combined organic layers
  5. concentrationconcentrate in vacuo
  6. customPurify the residue
  7. extractionin solid phase extraction (SPE) cartridge (Oasis™)
  8. customby HPLC to obtain a white solid, 8 mg, 10% yield

Sources & evidence

ORD record
ord-5df903008db34f00bf45a3acfb9a4547
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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