Hydrochloric Acid → HCID 87546674, compound

HRID 1435692Notes

Reaction equation

HRID 1435692 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([CH3:22])=[C:6]([S:10]([NH:13][C:14]2[S:15][CH:16]=[C:17]([CH2:19][CH2:20][OH:21])[N:18]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1.I[CH:24]([CH3:26])[CH3:25].Cl>C1COCC1.O>[Cl:3][C:4]1[C:5]([CH3:22])=[C:6]([S:10]([NH:13][C:14]2[S:15][CH:16]=[C:17]([CH2:19][CH2:20][O:21][CH:24]([CH3:26])[CH3:25])[N:18]=2)(=[O:11])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6362Isopropyl iodide2×HCID 24758Sodium hydride2×HCID 87545745HCID 87545745, compound

Product 1

HCID 87546674HCID 87546674, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (95% dry, 129 mg, 5.39 mmol) was added to a stirred solution of EXAMPLE 181A (359 mg, 1.08 mmol) in THF (10 mL) at room temperature. After stirring for 15 min, the mixture was treated with 2-iodopropane (917 mg, 5.39 mmol). After two days at 50° C., additional sodium hydride (26 mg, 1.08 mmol) and 2-iodopropane (366 mg, 2.16 mmol) were added. After stirring for 1 h the reaction mixture was acidified with 2M HCl and water was added. The product was extracted with DCM and dried (sodium sulfate). Evaporation of the solvent gave a residue which was purified by flash chromatography on silica gel eluting with 4% acetone in DCM giving (15 mg, 4%) of an oil which solidified on standing: MS (Ionspray, [M+H]+) m/z 374.

Workup

  1. waitAfter two days at 50° C.
  2. stirringAfter stirring for 1 h the reaction mixture
  3. additionwas added
  4. extractionThe product was extracted with DCM
  5. dry with materialdried (sodium sulfate)
  6. customEvaporation of the solvent
  7. customgave a residue which
  8. customwas purified by flash chromatography on silica gel eluting with 4% acetone in DCM giving (15 mg, 4%) of an oil which

Sources & evidence

ORD record
ord-42a52183f22c4b8d837fbd4befa1db5a
Source dataset
uspto-grants-2009_11
Patent number
US07618961B2

Reaction notes

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