Ammonium Chloride → HCID 68463910, compound

HRID 1995010Notes

Reaction equation

HRID 1995010 reaction equation
[CH:1]([CH:3]1[S:7][C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][C:11]=3[N:17]([CH3:27])[S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)(=[O:20])=[O:19])=[N:5][CH2:4]1)=O.[ClH:28].[NH:29]1[CH2:33][CH2:32][C:31](=[O:34])[CH2:30]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl-].[NH4+]>O1CCCC1.C(N(CC)CC)C>[ClH:28].[ClH:28].[CH3:27][N:17]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[NH:9][C:8]([C:6]1[S:7][CH:3]([CH2:1][N:29]3[CH2:33][CH2:32][C:31](=[O:34])[CH2:30]3)[CH2:4][N:5]=1)=[CH:16]2)[S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)(=[O:20])=[O:19]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 5049666Sodium triacetoxyborohydrideHCID 19106857Pyrrolidin-3-one hydrochlorideHCID 57503229HCID 57503229, compound

Product 1

HCID 68463910HCID 68463910, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of N-[2-(5-formyl-4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-N-methylpyridine-2-sulfonamide (200 mg), pyrrolidin-3-one hydrochloride (120 mg), triethylamine (150 μL) and tetrahydrofuran (5 mL) was added sodium triacetoxyborohydride (210 mg), and the mixture was stirred at room temperature for 10 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 a colorless oil from a fraction eluted with ethyl acetate. The colorless oil was dissolved in ethyl acetate (3 mL), and 4N hydrogen chloride-ethyl acetate solution (1 mL) was added. The precipitated solid was collected by filtration, washed with diethyl ether, and dried to give the title compound (110 mg, yield 40%) as a yellow amorphous solid. MS: 470 (MH+).

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
  5. customto give a colorless oil from a fraction
  6. washeluted with ethyl acetate
  7. dissolutionThe colorless oil was dissolved in ethyl acetate (3 mL)
  8. addition4N hydrogen chloride-ethyl acetate solution (1 mL) was added
  9. filtrationThe precipitated solid was collected by filtration
  10. washwashed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-34a7d17ea17c4f6ebefd3f22175892ef
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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