Acetyl chloride → HCID 54711278, compound

HRID 1351353Notes

Reaction equation

HRID 1351353 reaction equation
C([O:9][C:10]1[C:15](=[O:16])[N:14]([CH3:17])[C:13]([CH:18]2[CH2:22][CH2:21][CH2:20][NH:19]2)=[N:12][C:11]=1[C:23]([O:25]C)=O)(=O)C1C=CC=CC=1.C(N(CC)CC)C.[C:34](Cl)(=[O:36])[CH3:35].[F:38][C:39]1[CH:46]=[CH:45][C:42]([CH2:43][NH2:44])=[CH:41][CH:40]=1>C(Cl)(Cl)Cl.CN1C(=O)CCC1>[C:34]([N:19]1[CH2:20][CH2:21][CH2:22][CH:18]1[C:13]1[N:14]([CH3:17])[C:15](=[O:16])[C:10]([OH:9])=[C:11]([C:23]([NH:44][CH2:43][C:42]2[CH:45]=[CH:46][C:39]([F:38])=[CH:40][CH:41]=2)=[O:25])[N:12]=1)(=[O:36])[CH3:35]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 17961816HCID 17961816, compound

Product 1

HCID 54711278HCID 54711278, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred solution of the product of Step 1 (1.0 eq.) in CHCl3, triethylamine (3.0 eq.) was added followed by the addition of acetyl chloride (1.5 eq.). The reaction was stirred at room temperature until the starting material was consumed as determined by MS analysis. The reaction mixture was concentrated and the crude product was used directly in the subsequent step without further purification. A solution of the crude product from above (1.0 eq.) in NMP was treated with 4-fluorobenzylamine (2.0 eq.). The solution was stirred at reflux until the reactants were consumed as determined by MS analysis. The title compound was obtained by RP-HPLC purification (C18, eluting with water and acetonitrile containing 0.1% trifluoroacetic acid) as a 4:1 mixture of rotamers by NMR.

Workup

  1. customwas consumed
  2. concentrationThe reaction mixture was concentrated
  3. customthe crude product was used directly in the subsequent step without further purification
  4. stirringThe solution was stirred
  5. temperatureat reflux until the reactants
  6. customwere consumed

Sources & evidence

ORD record
ord-d605ccc3a384499d9ee411f1fd12a679
Source dataset
uspto-grants-2007_05
Patent number
US07217713B2

Reaction notes

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