HCID 58063577, compound → HCID 58063545, compound

HRID 2035723Notes

Reaction equation

HRID 2035723 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]=[N:16][N:17]([CH:19]4[CH2:25][CH2:24][C:23]5[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=5[N:21]([CH2:30][C:31]([F:34])([F:33])[F:32])[C:20]4=[O:35])[CH:18]=3)=[CH:10][C:9]=2[O:36][CH3:37])[CH:5]=[CH:4][N:3]=1.[CH2:38]([Mg]Br)[CH3:39]>C1COCC1.CN1C(=O)CCC1>[CH2:38]([C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]=[N:16][N:17]([CH:19]4[CH2:25][CH2:24][C:23]5[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=5[N:21]([CH2:30][C:31]([F:34])([F:33])[F:32])[C:20]4=[O:35])[CH:18]=3)=[CH:10][C:9]=2[O:36][CH3:37])[CH:5]=[CH:4][N:3]=1)[CH3:39]

Participants

5

Reactant 2

HCID 58063577HCID 58063577, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 58063545HCID 58063545, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred suspension of 3-{4-[4-(2-chloropyridin-4-yl)-3-methoxyphenyl]-1H-1,2,3-triazol-1-yl}-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (50 mg, 0.095 mmol), previously prepared, and ferric acetylacetonate (3.34 mg, 9.47 μmol) in THF (852 μl) and NMP (95 μl) at 0° C. was added ethyl magnesium bromide (1M in THF, 189 μl, 0.189 mmol). The reaction was held at 0° C. and stirred for 15 minutes. The reaction was quenched at 0° C. with a small addition of 1 mL of a saturated NH4Cl aq. solution. The reaction was diluted with 50 mL of H2O and was extracted with 3×50 mL portions of DCM. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo Analytically pure material was obtained by purification by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.05% Formic Acid. Lyophilisation afforded 3-{4-[4-(2-ethylpyridin-4-yl)-3-methoxyphenyl]-1H-1,2,3-triazol-1-yl}-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1 benzazepin-2-one.

Workup

  1. custompreviously prepared
  2. customwas held at 0° C.
  3. customThe reaction was quenched at 0° C. with a small addition of 1 mL of a saturated NH4Cl aq. solution
  4. additionThe reaction was diluted with 50 mL of H2O
  5. extractionwas extracted with 3×50 mL portions of DCM
  6. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo Analytically pure material
  9. customwas obtained by purification by preparative HPLC Reverse phase (C-18)
  10. washeluting with acetonitrile/water+0.05% Formic Acid

Sources & evidence

ORD record
ord-39f2c951d67f44eabecb20413607fd76
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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