Ammonium Chloride → HCID 12015832, compound

HRID 842376Notes

Reaction equation

HRID 842376 reaction equation
C([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=2)[CH:10]=[N:9]1)(OC(C)(C)C)=O.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:28]([C:32]1[CH:37]=[CH:36][C:35]([C:38]2[O:39][C:40](=[O:47])[C:41]3[S:46][CH:45]=[CH:44][C:42]=3[N:43]=2)=[CH:34][CH:33]=1)([CH3:31])([CH3:30])[CH3:29].[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[C:28]([C:32]1[CH:37]=[CH:36][C:35]([C:38]([NH:43][C:42]2[CH:44]=[CH:45][S:46][C:41]=2[C:40]([NH:17][C:14]2[CH:15]=[C:16]3[C:11]([CH:10]=[N:9][NH:8]3)=[CH:12][CH:13]=2)=[O:47])=[O:39])=[CH:34][CH:33]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 10684544HCID 10684544, compoundHCID 120186071-BOC-6-AMINO-INDAZOLE

Product 1

HCID 12015832HCID 12015832, compoundYield 18.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 1-Boc-6-aminoindazole (100 mg, 0.43 mmol) in tetrahydrofuran (2 mL) at 0° C. was added a solution of potassium bis(trimethylsilyl)amide (180 mg, 0.90 mmol) in tetrahydrofuran (2 mL). After 15 min, this solution was transferred via syringe to a stirring solution of 2-(4-t-butylphenyl)-4-oxo-4H-thieno[3,2-d][1,3]oxazine (122 mg, 0.43 mmol) in tetrahydrofuran (2 mL). After 45 min, saturated ammonium chloride was added, the mixture was diluted with ethyl acetate, and the phases were separated. The aqueous phase was extracted 3 times with ethyl acetate. The combined ethyl acetate extracts were then washed once with brine, dried over magnesium sulfate, filtered, and the solvent removed in vacuo. The crude product was purified by column chromatography over silica gel using an eluent of 40% ethyl acetate in hexane and 50% ethyl acetate in hexane to afford the product (34 mg, 15%).

Workup

  1. waitAfter 45 min
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted 3 times with ethyl acetate
  4. washThe combined ethyl acetate extracts were then washed once with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe crude product was purified by column chromatography over silica gel using an eluent of 40% ethyl acetate in hexane and 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-f41c555ae1b04ed4b09dc49fd40aeab5
Source dataset
uspto-grants-2002_04
Patent number
US06372759B1

Reaction notes

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