Ammonium Chloride → HCID 9958543, compound

HRID 1060842Notes

Reaction equation

HRID 1060842 reaction equation
[CH3:1][O:2][C:3]1[CH:41]=[CH:40][C:6]([C:7]([N:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:15][CH:16]=3)[C:11]([CH2:23][C:24]3[CH:25]=[C:26]([CH:36]=[CH:37][CH:38]=3)[O:27][C@@H:28]([CH3:35])[C:29]([O:31]CC=C)=[O:30])=[C:10]2[CH3:39])=[O:8])=[CH:5][CH:4]=1.CC1(C)CC(=O)CC(=O)C1.C(N(CC)C(C)C)(C)C.[Cl-].[NH4+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][C:19]([F:20])([F:21])[F:22])=[CH:15][CH:16]=3)[C:11]([CH2:23][C:24]3[CH:25]=[C:26]([CH:36]=[CH:37][CH:38]=3)[O:27][C@@H:28]([CH3:35])[C:29]([OH:31])=[O:30])=[C:10]2[CH3:39])=[O:8])=[CH:40][CH:41]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 31358DimedoneHCID 81531DiisopropylethylamineHCID 12052587HCID 12052587, compound

Product 1

HCID 9958543HCID 9958543, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 6 (490 mg, 0.86 mmole) was dissolved in DMF (9 mL). 5,5-Dimethyl-1,3-cyclohexanedione (181 mg, 1.29 mmole), N,N-diisopropylethylamine (0.225 mL, 1.29 mmole) and (tetrakistriphenylphoshine)palladium (50 mg, 0.043 mmole) were then added and the solution stirred for 2 hours. Then aqueous ammonium chloride was added and the solution was extracted repeatedly with dichloromethane. The combined organics were dried over sodium sulfate, filtered and the filtrate was evaporated . The crude isolate was then purified by silica gel chromatography to give the title compound (395 mg, 87%).

Workup

  1. extractionthe solution was extracted repeatedly with dichloromethane
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customthe filtrate was evaporated
  5. customThe crude isolate
  6. customwas then purified by silica gel chromatography

Sources & evidence

ORD record
ord-a4f1bf715c02432796828b3948f3d213
Source dataset
uspto-grants-2003_02
Patent number
US06525083B2

Reaction notes

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