HCID 57631774, compound → HCID 57632060, compound

HRID 63762Notes

Reaction equation

HRID 63762 reaction equation
CON(C)[C:4]([C:6]1[CH:7]=[N:8][N:9]2[C:14]([CH3:16])([CH3:15])[CH2:13][CH:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:11]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:10]=12)=[O:5].[CH3:31][C:32]1[CH:40]=[CH:39][C:35]([CH2:36][Mg]Cl)=[CH:34][CH:33]=1>C1COCC1>[CH2:23]([N:11]1[CH:12]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:13][C:14]([CH3:16])([CH3:15])[N:9]2[N:8]=[CH:7][C:6]([C:4](=[O:5])[CH2:31][C:32]3[CH:40]=[CH:39][C:35]([CH3:36])=[CH:34][CH:33]=3)=[C:10]12)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 57631774HCID 57631774, compoundHCID 178425359HCID 178425359, compound

Product 1

HCID 57632060HCID 57632060, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 0.65 g (1.61 mmol) of 3 dissolved in 20 mL of THF was added 6.4 mL (3.2 mmol) of a 0.5 M solution of 4-methylbenzylmagnesium chloride in THF via syringe over 10 min. After stirring at room temperature for 1 h, the reaction was quenched by addition of approximately 2 mL of saturated aqueous ammonium chloride. The reaction was then diluted with AcOEt and dried over sodium sulfate. Filtering the solution through a short plug of silica gel and concentrating in vacuo provided the crude product as an oil. Purification of this oil by flash chromatography eluting with 75% hexanes/AcOEt gave 0.64 g (89%) of the title compound as a white foam. MS Calcd.: 449. Found: 450 (M+H).

Workup

  1. customthe reaction was quenched by addition of approximately 2 mL of saturated aqueous ammonium chloride
  2. additionThe reaction was then diluted with AcOEt
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltering the solution through a short plug of silica gel
  5. concentrationconcentrating in vacuo
  6. customprovided the crude product as an oil
  7. customPurification of this oil by flash chromatography
  8. washeluting with 75% hexanes/AcOEt

Sources & evidence

ORD record
ord-2c62dc13002a4f318261a260526e53ff
Source dataset
uspto-grants-2016_09
Patent number
US09447100B2

Reaction notes

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