Ammonium Chloride → HCID 71251262, compound

HRID 2171891Notes

Reaction equation

HRID 2171891 reaction equation
[Cl-].[NH4+:2].C[Al](C)C.[F:7][C:8]1[C:9]([NH:34][CH:35]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH2:36][C:37](OC)=O)=[N:10][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([F:23])[CH:21]=3)[N:16]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH:15]=2)=[N:12][CH:13]=1>C1(C)C=CC=CC=1>[F:7][C:8]1[C:9]([NH:34][CH:35]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH2:36][C:37]#[N:2])=[N:10][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([F:23])[CH:21]=3)[N:16]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH:15]=2)=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 71247857HCID 71247857, compound

Product 1

HCID 71251262HCID 71251262, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

Ammonium chloride (0.12 g, 2.30 mmol) was suspended in toluene (4.5 mL). The mixture was cooled in an ice bath and AlMe3 (1.15 mL of a 2 M solution in toluene, 2.30 mmol) was added dropwise. The mixture was stirred 30 minutes and another 30 min at room temperature. A solution of racemic methyl 3-[[5-fluoro-2-[5-fluoro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]amino]-4,4-dimethyl-pentanoate (0.25 g, 0.46 mmol) in 4.5 mL toluene was added and the resulting mixture was stirred 60° C. overnight. The reaction mixture was cooled in an ice bath and quenched with 1N HCl. The mixture was extracted with dichloromethane and filtered through a phase separator. The residue was purified on silica gel (EA/Hex): LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, RT=2.04 minutes (M+H) 511.42.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. stirringthe resulting mixture was stirred 60° C. overnight
  3. temperatureThe reaction mixture was cooled in an ice bath
  4. customquenched with 1N HCl
  5. extractionThe mixture was extracted with dichloromethane
  6. filtrationfiltered through a phase separator
  7. customThe residue was purified on silica gel (EA/Hex)
  8. customLCMS Gradient 10-90%, 0.1% formic acid, 5 minutes

Sources & evidence

ORD record
ord-7d00e08adae84c75a321a235827fe31f
Source dataset
uspto-grants-2015_06
Patent number
US09051319B2

Reaction notes

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