Water → HCID 73990582, compound

HRID 2415641Notes

Reaction equation

HRID 2415641 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:38]=[CH:37][CH:36]=[CH:35][C:10]=1[O:11][C:12]1[N:17]=[CH:16][N:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25](=[N:31][O:32][CH3:33])[C:26]([N:28]([OH:30])[CH3:29])=[O:27])[C:13]=1[F:34].[C:39](Cl)(=[O:41])[CH3:40].O>O1CCCC1>[C:39]([O:30][N:28]([CH3:29])[C:26](=[O:27])[C:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[O:18][C:14]1[C:13]([F:34])=[C:12]([O:11][C:10]2[CH:35]=[CH:36][CH:37]=[CH:38][C:9]=2[Cl:8])[N:17]=[CH:16][N:15]=1)=[N:31][O:32][CH3:33])(=[O:41])[CH3:40]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 73096493HCID 73096493, compound

Product 1

HCID 73990582HCID 73990582, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.12 g (0.0012 mol) of triethylamine is initially added to a mixture of 0.4 g (0.0009 mol) of 2-(2-{[6-(2-chlorophenoxy)-5-fluoro-4-pyrimidinyl]oxy}phenyl)-N-hydroxy-2-(methoxyimino)-N-methylacetamide in 20 ml of tetrahydrofuran, and 0.08 g (0.00099 mol) of acetyl chloride is then added and the mixture is stirred at room temperature for 1 hour. The reaction mixture is poured into 100 ml of water and extracted 3 times with in each case 50 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica gel using cyclohexane/ethyl acetate (4:1). This gives 0.18 g (41.1% of theory) of N-(acetyloxy)-2-(2-{[6-(2-chlorophenoxy)-5-fluoro-4-pyrimidinyl]oxy} phenyl)-2-(methoxyimino)-N-methylacetamide.

Workup

  1. additionis then added
  2. extractionextracted 3 times with in each case 50 ml of ethyl acetate
  3. dry with materialThe combined organic phases are dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-e8ae6f5093a24754993c654ac08ae6b7
Source dataset
uspto-grants-2004_11
Patent number
US06821927B1

Reaction notes

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