Lithium borohydride → HCID 59135669, compound

HRID 1994940Notes

Reaction equation

HRID 1994940 reaction equation
[CH3:1][N:2]([S:23]([C:26]1[S:27][CH:28]=[CH:29][N:30]=1)(=[O:25])=[O:24])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][C:18](OCC)=[O:19])[CH2:15][N:16]=1)=[CH:8]2.[BH4-].[Li+]>O1CCCC1.CO.C(OCC)(=O)C.Cl>[OH:19][CH2:18][CH2:17][CH:14]1[S:13][C:12]([C:9]2[NH:10][C:11]3[C:7]([CH:8]=2)=[CH:6][CH:5]=[CH:4][C:3]=3[N:2]([CH3:1])[S:23]([C:26]2[S:27][CH:28]=[CH:29][N:30]=2)(=[O:24])=[O:25])=[N:16][CH2:15]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-4cde5b4a4dd84fd1b44b470d2fb044f9
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

Loading…