Hydrochloric Acid → N-{5-(2-hydroxyethoxy)-2-[5-(thiomorpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylpyridine-2-sulfonamide

HRID 504942Notes

Reaction equation

HRID 504942 reaction equation
[CH3:1][N:2]([S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)(=[O:33])=[O:32])[C:3]1[CH:4]=[C:5]([O:24][CH2:25][C:26](OCC)=[O:27])[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][N:18]3[CH2:23][CH2:22][S:21][CH2:20][CH2:19]3)[CH2:15][N:16]=1)=[CH:8]2.[BH4-].[Li+].Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[OH:27][CH2:26][CH2:25][O:24][C:5]1[CH:6]=[C:7]2[C:11](=[C:3]([N:2]([CH3:1])[S:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=3)(=[O:32])=[O:33])[CH:4]=1)[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][N:18]3[CH2:23][CH2:22][S:21][CH2:20][CH2:19]3)[CH2:15][N:16]=1)=[CH:8]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 59136117ethyl({7-[methyl(pyridin-2-ylsulfonyl)amino]-2-[5-(thiomorpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-5-yl}oxy)acetate

Product 1

HCID 59135920N-{5-(2-hydroxyethoxy)-2-[5-(thiomorpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylpyridine-2-sulfonamideYield 55.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl ({7-[methyl(pyridin-2-ylsulfonyl)amino]-2-[5-(thiomorpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-5-yl}oxy)acetate (400 mg) in tetrahydrofuran (5 mL) was added lithium borohydride (18 mg) under ice-cooling, and the mixture was stirred at room temperature for 3 days. 1N Hydrochloric acid was added under ice-cooling, and the mixture was basified with saturated aqueous sodium hydrogencarbonate, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate to give the title compound (205 mg, yield 55%) as a colorless solid. melting point 160-162° C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-553bcb0dd0284870bdb62b0ccac1d04f
Source dataset
uspto-grants-2010_08
Patent number
US07777047B2

Reaction notes

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