Acetyl chloride → HCID 59525821, compound

HRID 385834Notes

Reaction equation

HRID 385834 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.[C:26](Cl)(=[O:28])[CH3:27]>ClCCl>[C:26]([N:9]([CH2:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=1)[CH2:10][C:11]([NH:13][CH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:12])(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 59526375HCID 59526375, compound

Product 1

HCID 59525821HCID 59525821, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

N2-[(6-Bromopyridin-2-yl)methyl]-N-cyclopentylglycinamide (Example 187, Step 1) (0.25 g, 0.80 mmol) was dissolved in dichloromethane (3.2 mL) and triethylamine (0.34 mL, 2.4 mmol) was added and the reaction was cooled to 0° C. Acetyl chloride (0.06 mL, 0.88 mmol) was added and the reaction was allowed to warm to room temperature and stir to completion. The solution was diluted with dichloromethane, washed with water, dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by reverse phase HPLC 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 residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-52fa2471da1644b295aa1f87b0662b8a
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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