Dimethylamine → HCID 53628646, compound

HRID 1260223Notes

Reaction equation

HRID 1260223 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C@@H:19]3[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH3:26])[CH2:20]3)=[CH:15][CH:14]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)=O.[CH3:27][NH:28][CH3:29].O1CCCC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl.O.C(O)(=O)C>[CH3:27][N:28]([CH2:1][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C@@H:19]3[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH3:26])[CH2:20]3)=[CH:15][CH:14]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)[CH3:29]

Participants

9

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 57470073HCID 57470073, compound

Product 1

HCID 53628646HCID 53628646, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

0.3 g of 4-formyl-N-[4-((S)-1-propyl-pyrrolidin-3-yl)-phenyl]-benzenesulfonamide (0.81 mmol) were dissolved in 20 ml of dichloromethane, 0.6 ml of a 2 M solution of dimethylamine in tetrahydrofuran (1.21 mmol) added, followed by addition of 0.07 ml of acetic acid and 0.256 g sodium triacetoxyborohydride. The reaction mixture was stirred for 15 h at room temperature, water added, the pH adjusted to alkaline conditions with 1 N aqueous sodium hydroxide, and the aqueous layer extracted twice with diethylether. The combined ether extracts were dried over magnesium sulfate, filtered and the solvent evaporated under reduced pressure. The crude product was purified via preparative HPLC on a 40 mm Deltapak column with methanol/water/0.1% acetic acid. Fractions containing the product were combined, the solvent evaporated and the product isolated after extraction of an alkaline aqueous layer. (0.051 g).

Workup

  1. extractionthe aqueous layer extracted twice with diethylether
  2. dry with materialThe combined ether extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent evaporated under reduced pressure
  5. customThe crude product was purified via preparative HPLC on a 40 mm Deltapak column with methanol/water/0.1% acetic acid
  6. additionFractions containing the product
  7. customthe solvent evaporated
  8. customthe product isolated
  9. extractionafter extraction of an alkaline aqueous layer

Sources & evidence

ORD record
ord-265716da97bc42479fe1830862f7ac69
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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