Sulfuric acid magnesium salt (1:1) → HCID 67185946, compound

HRID 735991Notes

Reaction equation

HRID 735991 reaction equation
[C:1]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][CH2:27][NH2:28].[O-]S([O-])(=O)=O.[Mg+2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.CO.C(Cl)Cl>[C:1]([C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH:28][CH2:27][CH2:26][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[F:19])=[CH:13][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

8

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 6433572-(2-Fluorophenyl)ethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 578413204-Dec-1-ynylbenzaldehyde

Product 1

HCID 67185946HCID 67185946, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-dec-1-ynylbenzaldehyde (24.2 mg, 0.1 mmol) in anhydrous THF (0.6 mL) was added the 2-(2-fluorophenyl)ethylamine (13.9 mg, 0.1 mmol) and anhydrous MgSO4 (50 mg). The mixture was stirred overnight at RT. The reaction mixture was filtered and evaporated to give an oily residue. This crude product was taken up in MeOH (0.5 mL) then the sodium triacetoxyborohydride (53 mg, 0.25 mmol) was added and the reaction mixture was stirred overnight at rt. The solvents were evaporated under vacuum to give a solid. This solid was suspended in DCM (0.75 mL) and eluted through a SCX column (Isolute, 1 g) with DCM (6 mL), then NH3 (2M in MeOH, 4 mL). The desired fractions (TLC monitoring) were concentrated under vacuum to afford the title product as a yellow oil. M+(LC/MS(ESI)): 366.3. HPLC (Condition A), Rt: 4.64 min (HPLC purity: 80.5%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. customto give an oily residue
  4. stirringthe reaction mixture was stirred overnight at rt
  5. customThe solvents were evaporated under vacuum
  6. customto give a solid
  7. washeluted through a SCX column (Isolute, 1 g) with DCM (6 mL)
  8. concentrationThe desired fractions (TLC monitoring) were concentrated under vacuum

Sources & evidence

ORD record
ord-0b32b788f1c84f06887999330635171e
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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