HCID 86671464, compound → HCID 68313073, compound

HRID 1530536Notes

Reaction equation

HRID 1530536 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 (3.5 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 by rotate evaporate. The residue was extracted with ethyl acetate (3×20 mL), washed with water (3×20 mL), and sat. NaCl (20 mL). The organic phase was dried and concentrated to give the crude product, which was purified by silica gel chromatography eluting with EtOAc/petroleum ether (1:1) to give 1-{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-pentaen-13-yl}ethan-1-one (560 mg, 80% yield) as a white solid. LCMS (ESI) m/z: 338.2 [M+H+]

Workup

  1. customAfter being quenched with aqueous NH4Cl (20 mL), most of THF
  2. customwas removed by rotate
  3. customevaporate
  4. extractionThe residue was extracted with ethyl acetate (3×20 mL)
  5. washwashed with water (3×20 mL), and sat. NaCl (20 mL)
  6. customThe organic phase was dried
  7. concentrationconcentrated
  8. customto give the crude product, which
  9. customwas purified by silica gel chromatography
  10. washeluting with EtOAc/petroleum ether (1:1)

Sources & evidence

ORD record
ord-22ba7a7e5f344015880060a26541ce28
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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