Acetyl chloride → HCID 46882621, compound

HRID 1990877Notes

Reaction equation

HRID 1990877 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[O:16][C:17]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)[CH3:2].[C:30](Cl)(=[O:32])[CH3:31].C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH2:7][N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[O:16][C:17]3[CH:23]=[CH:22][C:21]([NH:24][C:30](=[O:32])[CH3:31])=[CH:20][C:18]=3[N:19]=2)[CH2:12][CH2:13]1)[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 58706344HCID 58706344, compound

Product 1

HCID 46882621HCID 46882621, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N2-[1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-benzooxazole-2,5-diamine (39.8 mg, 0.1 mmol, 1.0 equiv) and acetyl chloride (0.009 mL, 7.9 mg, 0.1 mmol, 1.0 equiv) in anhydrous DMF (1 mL) was added diisopropylethylamine (23.4 μL, 25.9 mg, 0.2 mmol, 2.0 equiv) and the mixture stirred at 100° C. over night. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 8.1 mg (19%) of the title compound. MS (ESI): 439.5 [M+H]+.

Workup

  1. customRemoval of the solvent
  2. customunder reduced pressure and purification by preparative HPLC on reversed phase
  3. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-cd554a7ab70c41d588a8d17ed3c4b8b4
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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