Acetyl chloride → HCID 86655679, compound

HRID 2047481Notes

Reaction equation

HRID 2047481 reaction equation
Cl.Cl.[F:3][C:4]([F:41])([F:40])[C:5]1[CH:6]=[C:7]([N:15]([CH3:39])[C:16]([N:18]([C@@H:20]2[CH2:25][CH2:24][N:23]([CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[CH2:22][C@H:21]2[C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH3:19])=[O:17])[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1.C(N(CC)CC)C.[C:49]([Cl:52])(=[O:51])[CH3:50]>C(#N)C.C(OCC)(=O)C>[ClH:52].[C:49]([N:29]1[CH2:30][CH2:31][CH:26]([N:23]2[CH2:24][CH2:25][C@@H:20]([N:18]([CH3:19])[C:16]([N:15]([C:7]3[CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=[C:5]([C:4]([F:3])([F:40])[F:41])[CH:6]=3)[CH3:39])=[O:17])[C@H:21]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[CH2:22]2)[CH2:27][CH2:28]1)(=[O:51])[CH3:50]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86655681HCID 86655681, compound

Product 1

HCID 86655679HCID 86655679, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound (0.18 g) obtained in Example 81 and triethylamine (0.13 mL) in acetonitrile (6.0 mL) was added acetyl chloride (0.032 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH Chromatorex) (solvent gradient; 60→100% ethyl acetate/hexane) and treated with 2N hydrogen chloride/2-propanol to give the title compound (0.15 g, 80%) as a white powder.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (NH Chromatorex) (solvent gradient; 60→100% ethyl acetate/hexane)
  5. additiontreated with 2N hydrogen chloride/2-propanol

Sources & evidence

ORD record
ord-7ac9c43b09304489aa2e6d0941d4abd9
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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