Ammonium Chloride → HCID 90449791, compound

HRID 1411326Notes

Reaction equation

HRID 1411326 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15](=[O:22])[CH2:16][C:17](OCC)=[O:18])[CH2:11]3)[CH2:9][N:8]([C:23](=[O:31])[NH:24][C:25]3[S:26][C:27]([Cl:30])=[CH:28][N:29]=3)[C:5]2=[CH:6][CH:7]=1.[BH4-].[Na+].[Cl-].[NH4+]>O1CCCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15](=[O:22])[CH2:16][CH2:17][OH:18])[CH2:11]3)[CH2:9][N:8]([C:23]([NH:24][C:25]3[S:26][C:27]([Cl:30])=[CH:28][N:29]=3)=[O:31])[C:5]2=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 90449839HCID 90449839, compound

Product 1

HCID 90449791HCID 90449791, compoundYield 49.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-(5-chloro-1-((5-chlorothiazol-2-yl)carbamoyl)spiro[indoline-3,3′-pyrrolidin]-1′-yl)-3-oxopropanoate (62.1 mg, 0.128 mmol) was dissolved in tetrahydrofuran (5 mL) and methanol (5 mL). Thereafter, sodium borohydride (150 mg, 3.97 mmol) was added to the above obtained solution at room temperature, and the thus obtained mixture was then stirred for 2 hours while heating under reflux. Thereafter, a saturated aqueous solution of ammonium chloride was 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=10:1) to obtain the captioned compound (28.2 mg, 49%) in the form of a white amorphous product.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  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=10:1)

Sources & evidence

ORD record
ord-f37d2a559ad44378a91a1cd18660a7ab
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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