Ammonium Chloride → N-{2-[8-(2-hydroxy-2-methylpropyl)-1-thia-3,8-diazaspiro[4.5]dec-2-en-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide

HRID 1960547Notes

Reaction equation

HRID 1960547 reaction equation
[CH3:1][N:2]([S:27]([C:30]1[S:31][CH:32]=[CH:33][CH:34]=1)(=[O:29])=[O:28])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][C:14]3([CH2:21][CH2:20][N:19]([CH2:22]C(OC)=O)[CH2:18][CH2:17]3)[CH2:15][N:16]=1)=[CH:8]2.[CH3:35][Li].C([O:39][CH2:40][CH3:41])C.[Cl-].[NH4+]>O1CCCC1>[OH:39][C:40]([CH3:41])([CH3:35])[CH2:22][N:19]1[CH2:20][CH2:21][C: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:27]([C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)(=[O:29])=[O:28])=[N:16][CH2:15]2)[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 59136018methyl (2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1-thia-3,8-diazaspiro[4.5]dec-2-en-8-yl)acetateHCID 178467906HCID 178467906, compound

Product 1

HCID 59135975N-{2-[8-(2-hydroxy-2-methylpropyl)-1-thia-3,8-diazaspiro[4.5]dec-2-en-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamideYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1-thia-3,8-diazaspiro[4.5]dec-2-en-8-yl)acetate (211 mg) in tetrahydrofuran (3 mL) was added 1.5M methyllithium-diethyl ether solution (2 mL) at room temperature, and the mixture was stirred for 30 min. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography to give the title compound (92 mg, yield 44%) as white crystals from a fraction eluted with ethyl acetate:hexane=1:3. melting point 191° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-94c7f88f2d134da38b5ec10c5e79f517
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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