Hydrochloric Acid → HCID 86652851, compound

HRID 1188974Notes

Reaction equation

HRID 1188974 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([O:30][C:31]3[CH:36]=[CH:35][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:33][CH:32]=3)[CH:13]=[C:14]3[C:18]=2[NH:17][C:16]([C:19]2[S:20][CH:21]([CH2:24][C:25](OCC)=[O:26])[CH2:22][N:23]=2)=[CH:15]3)[CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+].Cl.C(OCC)(=O)C>O1CCCC1.CCCCCC>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([O:30][C:31]3[CH:32]=[CH:33][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:35][CH:36]=3)[CH:13]=[C:14]3[C:18]=2[NH:17][C:16]([C:19]2[S:20][CH:21]([CH2:24][CH2:25][OH:26])[CH2:22][N:23]=2)=[CH:15]3)[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 86652852HCID 86652852, compound

Product 1

HCID 86652851HCID 86652851, compoundYield 20.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Ethyl (2-{7-[(6-chloropyridin-2-yl)methoxy]-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (400 mg) was dissolved in tetrahydrofuran (8 mL), lithium borohydride (43 mg) was added under ice-cooling, and the mixture was stirred at room temperature for 17 hr. 1M Hydrochloric acid was added to the reaction mixture, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtrated, and concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (ethyl acetate:hexane=40:60 to 100:0, volume ratio) to give the title compound (75 mg, yield 20%) as an amorphous solid. The amorphous solid was crystallized from diethyl ether to give pale-yellow crystals. melting point 93-94° C. MS 558 (MH+).

Workup

  1. temperaturecooling
  2. extractionthe mixture was subjected to extraction with ethyl acetate
  3. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained crude product

Sources & evidence

ORD record
ord-94da5ece28ea4867b190a568da2b34e0
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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