Ammonium Chloride → HCID 68739481, compound

HRID 240757Notes

Reaction equation

HRID 240757 reaction equation
CON(C)[C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[CH:9]2)=[O:5].[CH2:16]([Mg]Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl-].[NH4+]>O1CCCC1>[NH:11]1[C:12]2[C:8](=[CH:7][C:6]([C:4](=[O:5])[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][CH:13]=2)[CH:9]=[N:10]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 62814299N-methoxy-N-methyl-1H-indazole-5-carboxamideHCID 178418336HCID 178418336, compound3×

Product 1

HCID 68739481HCID 68739481, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Example 75B (900 mg, 4.39 mmol) in tetrahydrofuran (10 mL) was cooled under argon with an ice bath and treated with a 2M solution of benzyl magnesium chloride in tetrahydrofuran (6.6 mL, 13.16 mmol). The reaction was stirred overnight at room temperature followed by the addition of one more equivalent of benzyl magnesium chloride. The mixture was heated at 70° C. for 9 hours. One more equivalent of benzylmagnesium chloride was added, and the reaction was heated at 70° C. for another 90 minutes and was allowed to cool to room temperature. Aqueous saturated ammonium chloride was added, and the product was extracted with ethyl acetate and purified by silica gel column chromatography using 30% ethyl acetate in hexanes to afford the title compound. MS (ESI+) m/z 237.1 (M+H)+.

Workup

  1. temperatureThe mixture was heated at 70° C. for 9 hours
  2. temperaturethe reaction was heated at 70° C. for another 90 minutes
  3. temperatureto cool to room temperature
  4. extractionthe product was extracted with ethyl acetate
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-0869cf7e01dc41c8aa2a73e061bf4444
Source dataset
uspto-grants-2014_02
Patent number
US08648069B2

Reaction notes

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