Triethylamine → HCID 59525667, compound

HRID 385830Notes

Reaction equation

HRID 385830 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][NH:9][CH2:10][C:11]([NH:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:12])[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]([S:27]([CH3:26])(=[O:29])=[O:28])[CH2:10][C:11]([NH:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:12])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59526375HCID 59526375, compound

Product 1

HCID 59525667HCID 59525667, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

N2-[(6-Bromopyridin-2-yl)methyl]-N-cyclopentylglycinamide (0.25 g, 0.80 mmol) was dissolved in dichloromethane (3.2 mL) and triethylamine (0.34 mL, 2.4 mmol) was added. The reaction was cooled to 0° C. and methanesulfonyl chloride (0.069 mL, 0.88 mmol) was added and the reaction was allowed to warm to room temperature. The solution was diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated. The crude mixture was purified by silica gel chromatography to yield the title compound.

Workup

  1. temperatureto warm to room temperature
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-bc87cba1e02b47a7a5dfd8f0e0a99b56
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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