Lithium borohydride → HCID 59135669, compound

HRID 1960506Notes

Reaction equation

HRID 1960506 reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]1[S:10][C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[N:20]([CH3:29])[S:21]([C:24]2[S:25][CH:26]=[CH:27][N:28]=2)(=[O:23])=[O:22])=[N:8][CH2:7]1)C.[BH4-].[Li+]>O1CCCC1.CO.C(OCC)(=O)C.Cl>[OH:3][CH2:4][CH2:5][CH:6]1[S:10][C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[N:20]([CH3:29])[S:21]([C:24]2[S:25][CH:26]=[CH:27][N:28]=2)(=[O:22])=[O:23])=[N:8][CH2:7]1

Participants

7

Reactant 2

HCID 4148881Lithium borohydrideHCID 59136014HCID 59136014, compound

Product 1

HCID 59135669HCID 59135669, compoundYield 14%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl(2-{7-[methyl(1,3-thiazol-2-ylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (200 mg) was dissolved in a mixed solvent of tetrahydrofuran (5 mL) and methanol (5 mL), and the mixture was cooled to 0° C. Lithium borohydride (20 mg) was added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate (100 mL) and 1N hydrochloric acid (50 mL). The organic layer was dried over sodium sulfate, and filtrated, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (25 mg, yield 14%) as a pale-Yellow solid. MS:423(MH+).

Workup

  1. dry with materialThe organic layer was dried over sodium sulfate
  2. filtrationfiltrated
  3. concentrationthe filtrate was concentrated
  4. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-95011c4bb55148b1b4940469b8c428eb
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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