Ammonium Chloride → HCID 58504033, compound

HRID 2407799Notes

Reaction equation

HRID 2407799 reaction equation
[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=[CH:5][C:4]([C:7]([N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:13][CH2:12]2)([C:9]#N)[CH3:8])=[CH:3][CH:2]=1.C[Mg]Br.[Cl-].[NH4+]>O1CCCC1.C(OCC)C>[C:1]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:2]=[CH:3][C:4]([C:7]([N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:13][CH2:12]2)([CH3:8])[CH3:9])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 58503934HCID 58503934, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58504033HCID 58504033, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound prepared in Example 363 (0.112 g) in tetrahydrofuran (3 mL) at 0° C. was added a 3.0 M solution of methylmagnesium bromide in diethyl ether (0.27 mL), and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was poured onto cold saturated ammonium chloride, and the mixture was extracted with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexanes:triethylamine=80:20:1) to obtain the title compound (0.035 g) having the following physical data.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organics were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexanes:triethylamine=80:20:1)

Sources & evidence

ORD record
ord-b04c5e073dad4d2e93dc0677bc63d73a
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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