Ammonium Chloride → HCID 59625595, compound

HRID 2192850Notes

Reaction equation

HRID 2192850 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:8]([C:17]([N:19]([CH2:39][CH:40]([CH3:42])[CH3:41])[C@H:20]2[CH2:25][C@@H:24]([C:26](=[O:31])N(OC)C)[CH2:23][N:22]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:21]2)=[O:18])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:43][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[C:26]([C@@H:24]1[CH2:25][C@H:20]([N:19]([C:17]([C:8]2[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])=[N:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:6][CH:7]=2)=[O:18])[CH2:39][CH:40]([CH3:42])[CH3:41])[CH2:21][N:22]([C:32]([O:34][C:35]([CH3:38])([CH3:36])[CH3:37])=[O:33])[CH2:23]1)(=[O:31])[CH3:43]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 59625437HCID 59625437, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59625595HCID 59625595, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

tert-Butyl (3S,5R)-3-[({2-tert-butyl-4-[(3-methoxypropyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]-5-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate (75 mg) was dissolved in tetrahydrofuran (10 ml), 1 M methylmagnesium bromide in THF solution (1.3 ml) was added at 0° C., and the mixture was stirred at room temperature for 10 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (0:1-1:1) was concentrated under reduced pressure to give the object compound (38 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe fraction eluted with ethyl acetate-hexane (0:1-1:1)
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-7073104522384890bccc9f627e9d6b7e
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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