Methyl iodide → HCID 18617801, compound

HRID 1264245Notes

Reaction equation

HRID 1264245 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]#[C:11][C:12]1[CH:41]=[CH:40][C:15]([C:16]([NH:18][CH2:19][CH2:20][C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:25]=[C:24]3[C:37](=S)[NH2:38])=[O:17])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CI.C([O-])(=O)C.[NH4+:48]>CC(C)=O.CO>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]#[C:11][C:12]1[CH:41]=[CH:40][C:15]([C:16]([NH:18][CH2:19][CH2:20][C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:25]=[C:24]3[C:37](=[NH:48])[NH2:38])=[O:17])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 517165Ammonium AcetateHCID 18617851HCID 18617851, compound

Product 1

HCID 18617801HCID 18617801, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

t-Butyl 5-[2-[4-(3-t-butoxycarbonylaminoprop-1-ynyl)-benzoylamino]ethyl}-3-thiocarbamoyl-indole-1-carboxylate (73 mg, 0.13 mmol, reference example 78) is dissolved in acetone (75 mL) and methyl iodide (5 mL) added. This mixture is heated to reflux. After 15 minutes, the solvent is removed in vacuo giving a yellow residue. MS (ion spray) m/e 591 (M+H+). The residue (80 mg, 0.13 mmol) is dissolved in MeOH (15 mL) and ammonium acetate (0.5 g) added and this mixture heated at reflux for 20 minutes. The solvent is removed in vacuo and the residue partitioned between CH2Cl2 and water. The aqueous layer is extracted with CH2Cl2 and the combined organic layers washed with water, dried over magnesium sulfate and concentrated in vacuo. The crude product is purified by reverse phase HPLC eluting with 30-70%/15 minutes, giving 22 mg. MS (ion spray) m/z 560 (M+H+).

Workup

  1. temperatureThis mixture is heated to reflux
  2. customthe solvent is removed in vacuo
  3. customgiving a yellow residue
  4. temperaturethis mixture heated
  5. temperatureat reflux for 20 minutes
  6. customThe solvent is removed in vacuo
  7. customthe residue partitioned between CH2Cl2 and water
  8. extractionThe aqueous layer is extracted with CH2Cl2
  9. washthe combined organic layers washed with water
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated in vacuo
  12. customThe crude product is purified by reverse phase HPLC
  13. washeluting with 30-70%/15 minutes
  14. customgiving 22 mg

Sources & evidence

ORD record
ord-6c02466e2299458eb1ffb025ac99dd06
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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