Methyl iodide → HCID 22644780, compound

HRID 1976497Notes

Reaction equation

HRID 1976497 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[CH2:8]([O:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([N:22]2[CH:28]([C:29]([NH:31][OH:32])=[O:30])CCNCC2)(=[O:21])=[O:20])=[CH:15][CH:14]=1)[C:9]#[C:10][CH3:11].IC>CO.ClCCl.O>[CH2:8]([O:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([N:22]2[CH:28]([C:29]([NH:31][OH:32])=[O:30])[CH2:7][CH2:6][N:3]([CH3:1])[CH2:4][CH2:5]2)(=[O:20])=[O:21])=[CH:15][CH:14]=1)[C:9]#[C:10][CH3:11]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 8471Triethylamine2×HCID 11394505HCID 11394505, compound2×

Product 1

HCID 22644780HCID 22644780, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (0.08 mL) was added to a suspension of the product of Example 292, 4-{[4-(2-butynyloxy)phenyl]sulfonyl}-N-hydroxy-1,4-diazepane-5-carboxamide (0.10 g), in methanol (6 mL) to give a solution which was cooled to 0° C. lodomethane (0.025 mL) was then added. After 30 min the reaction mixture was allowed to warm to 25 ° C. After 20 min additional iodomethane (0.02 mL) was added followed by additional triethylamine (0.015 mL). After 18hours the reaction mixture was diluted with dichloromethane and water. The aqueous phase was washed with dichloromethane (3×). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. The material obtained was combined with material from a previous reaction run on the same scale and chromatographed on silica gel to give 4-{[4-(2-butynyloxy)phenyl]sulfonyl}-N-hydroxy-1-methyl-1,4-diazepane-5-carboxamide (0.067 g). Electrospray Mass Spec 382.2 (N+H)+

Workup

  1. customto give a solution which
  2. additionwas then added
  3. temperatureto warm to 25 ° C
  4. washThe aqueous phase was washed with dichloromethane (3×)
  5. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe material obtained
  8. customchromatographed on silica gel

Sources & evidence

ORD record
ord-273da85c363446aabc55b406c36ea206
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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