Acetic Acid → HCID 44242106, compound

HRID 1808141Notes

Reaction equation

HRID 1808141 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([NH2:18])[C:12]2[S:13][CH:14]=[C:15]([CH3:17])[N:16]=2)=[CH:2]1.[CH3:19][N:20]([CH3:34])[C:21]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O)(=O)C>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([NH:18][CH:24]2[CH2:23][CH2:22][C:21]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)([N:20]([CH3:34])[CH3:19])[CH2:26][CH2:25]2)[C:12]2[S:13][CH:14]=[C:15]([CH3:17])[N:16]=2)=[CH:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24436Sodium SulfateHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-oneHCID 42078449HCID 42078449, compound

Product 1

HCID 44242106HCID 44242106, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-2-(1H-indol-3-yl)-1-(4-methylthiazol-2-yl)ethylamine (500 mg, 1.94 mmol) and 4-dimethylamino-4-phenylcyclohexanone (421 mg, 1.94 mmol) in anhydrous tetrahydrofuran (40 mL) was mixed with sodium sulphate (1.00 g) and stirred for 3 h at room temperature. After adding acetic acid (291 mg, 287 μL, 4.85 mmol), sodium triacetoxyboron hydride (574 mg, 2.71 mmol) was added and the mixture stirred overnight at room temperature. The mixture was then filtered, the filtrate concentrated to low volume in a vacuum, the residue mixed with 1M potassium carbonate solution (50 mL) and extracted with ethyl acetate (3×30 mL). The combined organic phases were dried with sodium sulphate and concentrated to low volume in a vacuum. The raw product (750 mg) was purified by flash chromatography (100 g, 20×4.0 cm) with ethyl acetate/methanol [97:3→9:1 and 1% NH3 in each case (33% in water)].

Workup

  1. additionwas added
  2. stirringthe mixture stirred overnight at room temperature
  3. filtrationThe mixture was then filtered
  4. concentrationthe filtrate concentrated to low volume in a vacuum
  5. additionthe residue mixed with 1M potassium carbonate solution (50 mL)
  6. extractionextracted with ethyl acetate (3×30 mL)
  7. dry with materialThe combined organic phases were dried with sodium sulphate
  8. concentrationconcentrated to low volume in a vacuum
  9. customThe raw product (750 mg) was purified by flash chromatography (100 g, 20×4.0 cm) with ethyl acetate/methanol [97:3→9:1 and 1% NH3 in each case (33% in water)]

Sources & evidence

ORD record
ord-64833f8ec6374d83bed798cd1dc56664
Source dataset
uspto-grants-2013_01
Patent number
US08357705B2

Reaction notes

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