Acetic Anhydride → HCID 57933980, compound

HRID 1950015Notes

Reaction equation

HRID 1950015 reaction equation
BrC1C=CC(O)=CC=1N(CC)CC1C=CC(OCCN2CCCCC2)=C(F)C=1.[C:29]([N:32]([CH2:44][C:45]1[CH:50]=[CH:49][C:48]([O:51][CH2:52][CH2:53][N:54]2[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]2)=[C:47]([F:60])[CH:46]=1)[C:33]1[CH:34]=[C:35]([O:40][C:41](=[O:43])[CH3:42])[CH:36]=[CH:37][C:38]=1[Br:39])(=O)[CH3:30].C(OC(=O)C)(=O)C.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[Br:39][C:38]1[CH:37]=[CH:36][C:35]([O:40][C:41](=[O:43])[CH3:42])=[CH:34][C:33]=1[N:32]([CH2:29][CH3:30])[CH2:44][C:45]1[CH:50]=[CH:49][C:48]([O:51][CH2:52][CH2:53][N:54]2[CH2:55][CH2:56][CH2:57][CH2:58][CH2:59]2)=[C:47]([F:60])[CH:46]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 57934161HCID 57934161, compoundHCID 66627759HCID 66627759, compound

Product 1

HCID 57933980HCID 57933980, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To the total amount of 4-bromo-3-{ethyl[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl]amino}phenol crude product, which was synthesized from acetic acid 3-{acetyl-[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl]amino}-4-bromophenyl ester (300 mg) synthesized according to an analogous synthetic method to Example 337 described below, were added pyridine (3 ml) and acetic anhydride (3 ml), and the solution was stirred overnight at room temperature. To reaction mixture was added a saturated aqueous solution of sodium bicarbonate, the solution was extracted with ethyl acetate, then washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform-methanol system) to provide the title compound (200 mg).

Workup

  1. customsynthesized
  2. customTo reaction mixture
  3. extractionthe solution was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (chloroform-methanol system)

Sources & evidence

ORD record
ord-3405591e31d74d4a962e86a9c5e11daa
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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