Sodium Bicarbonate → N-[2-(5-{[2-(hydroxymethyl)-1H-imidazol-1-yl]methyl}-4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-N-methylpyridine-2-sulfonamide

HRID 1960571Notes

Reaction equation

HRID 1960571 reaction equation
[CH3:1][N:2]([S:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)(=[O:30])=[O:29])[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][N:18]3[CH:22]=[CH:21][N:20]=[C:19]3[C:23](OCC)=[O:24])[CH2:15][N:16]=1)=[CH:8]2.[BH4-].[Li+].C(=O)([O-])O.[Na+]>O1CCCC1.CO>[OH:24][CH2:23][C:19]1[N:18]([CH2:17][CH:14]2[S:13][C:12]([C:9]3[NH:10][C:11]4[C:7]([CH:8]=3)=[CH:6][CH:5]=[CH:4][C:3]=4[N:2]([CH3:1])[S:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)(=[O:29])=[O:30])=[N:16][CH2:15]2)[CH:22]=[CH:21][N:20]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 4148881Lithium borohydride2×HCID 59135802ethyl 1-[(2-{7-[methyl(pyridin-2-ylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)methyl]-1H-imidazole-2-carboxylate

Product 1

HCID 59135809N-[2-(5-{[2-(hydroxymethyl)-1H-imidazol-1-yl]methyl}-4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-N-methylpyridine-2-sulfonamideYield 19%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-[(2-{7-[methyl(pyridin-2-ylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)methyl]-1H-imidazole-2-carboxylate (220 mg) was dissolved in a mixed solvent of tetrahydrofuran (8 mL) and methanol (4 mL), lithium borohydride (27 mg) was added, and the mixture was stirred at room temperature for 1 hr. Lithium borohydride (20 mg) was added, and the mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtrated, and the filtrate was concentrated under reduced pressure. The residue was silica gel column chromatography (methanol:ethyl acetate=0:100-15:85) to give the title compound (38 mg, yield 19%) as a white solid. MS: 482(MH+).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 24 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltrated
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e688b526d1574cbaafa14ebf3b00b10f
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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