O-ethylhydroxylamine hydrochloride → HCID 11326327, compound

HRID 2102411Notes

Reaction equation

HRID 2102411 reaction equation
Cl.[CH2:2]([O:4][NH2:5])[CH3:3].C([O:8][C:9]([C:11]1[C:16]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][C:19]=2[F:26])=[C:15]([CH3:27])[N:14]2[N:28]=[CH:29][CH:30]=[C:13]2[N:12]=1)=O)C.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[CH2:2]([O:4][NH:5][C:9]([C:11]1[C:16]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][C:19]=2[F:26])=[C:15]([CH3:27])[N:14]2[N:28]=[CH:29][CH:30]=[C:13]2[N:12]=1)=[O:8])[CH3:3]

Participants

5

Reactant 3

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 2733832Lithium HexamethyldisilazideHCID 69009937HCID 69009937, compound

Product 1

HCID 11326327HCID 11326327, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

O-Ethyl-hydroxylamine HCl salt (2.50 equivalents) is added to a solution of 6-(2-fluoro-4-methylsulfanyl-phenylamino)-7-methylpyrazolo[1,5-a]pyrimidine-5-carboxylic acid ethyl ester (1.00 equivalent) in THF. The solution is cooled to 0° C. and lithium bis(trimethylsilyl)amide (6.00 equivalents, 1.0 M solution in hexanes) is added dropwise. The reaction mixture is warmed to room temperature. After stirring for 1 hour, the reaction is quenched by addition of a saturated aqueous solution of NaHCO3 and partitioned between EtOAc and brine. The aqueous layer is re-extracted with EtOAc. The combined organic extracts is dried (MgSO4) and concentrated. The product is purified by flash chromatography as necessary.

Workup

  1. temperatureThe reaction mixture is warmed to room temperature
  2. customthe reaction is quenched by addition of a saturated aqueous solution of NaHCO3
  3. custompartitioned between EtOAc and brine
  4. extractionThe aqueous layer is re-extracted with EtOAc
  5. dry with materialThe combined organic extracts is dried (MgSO4)
  6. concentrationconcentrated
  7. customThe product is purified by flash chromatography as necessary

Sources & evidence

ORD record
ord-29d90103cc844203bbd9231153509db3
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

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