HCID 86671464, compound → HCID 68313073, compound

HRID 1530543Notes

Reaction equation

HRID 1530543 reaction equation
CON(C)[C:4]([C:6]1[CH:19]=[C:18]2[C:9]([O:10][CH2:11][CH2:12][N:13]3[C:17]2=[N:16][C:15]([C:20]2[N:24]([CH:25]([CH3:27])[CH3:26])[N:23]=[CH:22][N:21]=2)=[CH:14]3)=[CH:8][CH:7]=1)=[O:5].[CH3:29][Mg]Cl>C1COCC1>[CH3:27][CH:25]([N:24]1[C:20]([C:15]2[N:16]=[C:17]3[N:13]([CH:14]=2)[CH2:12][CH2:11][O:10][C:9]2[C:18]3=[CH:19][C:6]([C:4](=[O:5])[CH3:29])=[CH:7][CH:8]=2)=[N:21][CH:22]=[N:23]1)[CH3:26]

Participants

4

Reactant 2

HCID 86671464HCID 86671464, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 68313073HCID 68313073, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-methoxy-N-methyl-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene-13-carboxamide (800 mg, 2.09 mmol) in THF (80 mL) was added methylmagnesium chloride (3.50 mL, 10.5 mmol) dropwise at 0° C. The mixture was further stirred at 0° C. for 1 h. After being quenched with aqueous NH4Cl (20 mL), most of THF was removed. The residue was extracted with ethyl acetate (3×20 mL), washed with water (3×20 mL), and brine (20 mL). The organic phase was dried and concentrated to give the crude product, which was purified by silica gel chromatography using 50% EtOAc in petroleum ether as eluant to give the desired product (560 mg, 80% yield) as a white solid. LCMS m/z [M+H]+ 338.2

Workup

  1. customAfter being quenched with aqueous NH4Cl (20 mL), most of THF
  2. customwas removed
  3. extractionThe residue was extracted with ethyl acetate (3×20 mL)
  4. washwashed with water (3×20 mL), and brine (20 mL)
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-a5d8db899112477eada5a54f6f4e91b5
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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