Sulfuric acid magnesium salt (1:1) → HCID 49871231, compound

HRID 1453166Notes

Reaction equation

HRID 1453166 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]2([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[O:17][C:16](=[O:18])[CH2:15][C:14](=[O:19])[CH2:13]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH3:25][C:26]1[CH:31]=[C:30]([CH3:32])[N:29]2[N:33]=[C:34]([CH:36]=O)[N:35]=[C:28]2[N:27]=1.[Al+3].[Cl-].[Cl-].[Cl-].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]2([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[O:17][C:16](=[O:18])[CH:15]([CH2:36][C:34]3[N:35]=[C:28]4[N:27]=[C:26]([CH3:25])[CH:31]=[C:30]([CH3:32])[N:29]4[N:33]=3)[C:14](=[O:19])[CH2:13]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 6451240Aluminum(III) ChlorideHCID 160761096-(3-chloro-4-methoxyphenethyl)-6-cyclopentyl-dihydro-3H-pyran-2,4-dioneHCID 236352265,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde

Product 1

HCID 49871231HCID 49871231, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6-[2-(3-Chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione from Step 1 below (1 g, 2.90 mmol) was combined with 5,7-Dimethyl-[1,2,4]triazolo[1,5-α]pyrimidine-2-carbaldehyde (0.5 g, 2.90 mmol) (described in Step 3 of example B(75)) in dry THF (15 mL) with magnetic stirring. To this solution was added AlCl3 (0.76 g, 5.81 mmol) as a soln in THF (6 mL) dropwise over 1 min. The resulting yellow solution was stirred at room temperature for 3 hours. The reaction was quenched with solid Na2CO3.10H2O (1.63 g, 5.81 mmol) and stirred at room temperature for 10 min. Next, the mixture was treated with MgSO4 (2.5 g) and the slurry allowed to stand for 1.5 hours. The yellow mixture was filtered through celite and the filtrate was concentrated. The crude residue was dissolved in EtOAc (50 mL) and treated with PtO2 and stirred with H2 (one balloon pressure). This was maintained for 1 hour then filtered through celite. The filtrate was concentrated and the residue chromatographed on silica gel eluting with CH2Cl2 through 0.75% MeOH in CH2Cl2 to yield the title compound as a white solid. 1H NMR (CDCl3): δ 1.37-1.85 (brm, 8H), 1.98 (m, 2H), 2.37 (m, 1H), 2.49-2.80 (m, 11H), 3.86 (s, 3H), 4.05 (d, J=15.6 Hz, 1H), 4.12 (d, J=15.6 Hz, 1H), 6.81 (d, J=8.6 Hz, 1H), 6.85 (s, 1H), 7.00 (d, J=8.6 Hz, 1H), 7.12 (s, 1H). Anal. Calcd. For C27H31ClN4O4: C, 63.46; H, 6.11; N, 10.96. Found: C, 63.23; H, 6.27; N, 10.74.

Workup

  1. stirringstirred at room temperature for 10 min
  2. waitto stand for 1.5 hours
  3. filtrationThe yellow mixture was filtered through celite
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe crude residue was dissolved in EtOAc (50 mL)
  6. additiontreated with PtO2
  7. stirringstirred with H2 (one balloon pressure)
  8. temperatureThis was maintained for 1 hour
  9. filtrationthen filtered through celite
  10. concentrationThe filtrate was concentrated
  11. customthe residue chromatographed on silica gel eluting with CH2Cl2 through 0.75% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-3d5a0027590e4f40bc1c0a14e8bf2556
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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