Ammonium Chloride → HCID 131732216, compound

HRID 1411298Notes

Reaction equation

HRID 1411298 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:24]C(C)([O-])C.[K+].[C:30]([N:33]1[CH2:37][CH2:36][C:35]2([C:45]3[C:40](=[CH:41][CH:42]=[C:43](C=O)[CH:44]=3)[N:39]([C:48]([NH:50][C:51]3[S:52][C:53]([Cl:56])=[CH:54][N:55]=3)=[O:49])[CH2:38]2)[CH2:34]1)(=[O:32])[CH3:31].[Cl-].[NH4+]>O1CCCC1.O>[C:30]([N:33]1[CH2:37][CH2:36][C:35]2([C:45]3[C:40](=[CH:41][CH:42]=[C:43]([CH:24]=[CH:4][O:3][CH3:2])[CH:44]=3)[N:39]([C:48]([NH:50][C:51]3[S:52][C:53]([Cl:56])=[CH:54][N:55]=3)=[O:49])[CH2:38]2)[CH2:34]1)(=[O:32])[CH3:31]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 90449869HCID 90449869, compound

Product 1

HCID 131732216HCID 131732216, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

(Methoxymethyl)triphenylphosphonium chloride (0.63 g, 1.85 mmol) was dissolved in tetrahydrofuran (4 mL). Thereafter, potassium tert-butoxide (0.21 g, 1.85 mmol) was added to the above obtained solution under cooling on ice, and the thus obtained mixture was then stirred for 10 minutes. Thereafter, a tetrahydrofuran solution (3 mL) of the 1′-acetyl-N-(5-chlorothiazol-2-yl)-5-formylspiro[indoline-3,3′-pyrrolidine]-1-carboxamide (100 mg, 0.247 mmol) obtained in Step 2 of Example 401 was added to the reaction solution, and the thus obtained mixture was then stirred at room temperature for 1 hour. Thereafter, a saturated aqueous solution of ammonium chloride and water were added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=30:1) to obtain 1′-acetyl-N-(5-chlorothiazol-2-yl)-5-(2-methoxyvinyl)spiro[indoline-3,3′-pyrrolidine]-1-carboxamide (83 mg, 78%) in the form of a yellow amorphous product.

Workup

  1. temperatureunder cooling on ice
  2. stirringthe thus obtained mixture was then stirred at room temperature for 1 hour
  3. extractionthe mixed solution was then extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. concentrationfollowed by concentration in vacuo
  7. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-6510652329d445b3a845e117c289ac64
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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