HCID 90449869, compound → HCID 90449833, compound

HRID 1411296Notes

Reaction equation

HRID 1411296 reaction equation
[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH:17]=[O:18])[CH:15]=3)[N:10]([C:19]([NH:21][C:22]3[S:23][C:24]([Cl:27])=[CH:25][N:26]=3)=[O:20])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2].[CH3:28][Mg]Br>O1CCCC1.[Cl-].[NH4+]>[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH:17]([OH:18])[CH3:28])[CH:15]=3)[N:10]([C:19]([NH:21][C:22]3[S:23][C:24]([Cl:27])=[CH:25][N:26]=3)=[O:20])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 90449869HCID 90449869, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 90449833HCID 90449833, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

The 1′-acetyl-N-(5-chlorothiazol-2-yl)-5-formylspiro[indoline-3,3′-pyrrolidine]-1-carboxamide (30.0 mg, 0.074 mmol) obtained in Step 2 of Example 401 was dissolved in tetrahydrofuran (1.4 mL). Thereafter, methyl magnesium bromide (1 M tetrahydrofuran solution, 224 μL) was added to the above obtained solution under cooling on ice, and the thus obtained mixture was then stirred at the same temperature as above for 1 hour. Thereafter, the reaction solution was diluted with a saturated aqueous solution of ammonium chloride, and was then extracted with chloroform. 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=10:1) to obtain the captioned compound (28.1 mg, 91%) in the form of a white solid.

Workup

  1. temperatureunder cooling on ice
  2. extractionwas then extracted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. concentrationfollowed by concentration in vacuo
  6. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-738a6fcca2b24484bb194d15dfa6fdd2
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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