Methanol → HCID 178432182, compound

HRID 1530123Notes

Reaction equation

HRID 1530123 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][N:5]2[C:12]=1[C:13]1[S:14][C:15]([C:24]2[N:28]=[CH:27][N:26](C3CCCCO3)[N:25]=2)=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1.FC(F)(F)C(O)=O.C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+].CO>>[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][N:5]2[C:12]=1[C:13]1[S:14][C:15]([C:24]2[NH:28][CH:27]=[N:26][N:25]=2)=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 58094904HCID 58094904, compound

Product 1

HCID 178432182HCID 178432182, compoundYield 48.7%

Procedure

2-Methyl-3-{4-phenyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-1,3-thiazol-2-yl}imidazo[1,2-a]pyridine-6-carbaldehyde (0.0300 g, 0.0638 mmol) was treated with Trifluoroacetic Acid (0.30 mL, 3.9 mmol) in Methylene chloride (1.5 mL, 23 mmol) at r.t. for 16 hours. The solvent and TFA were removed by purging with N2. The residue was treated with Potassium carbonate (82 mg, 0.59 mmol) in Methanol (2.0 mL, 49 mmol) at r.t. for 3 hours. The solvent was removed and the residue was suspended in 5% MeOH/DCM, filtered. The filtrate was purified by chromatograph in a 8 g AnaLogix column using MeOH/DCM (0/100 to 10/90) to afford a solid product (0.012 g, 48.7% yield). LCMS: (FA) ES+ 387, ES− 385. 1H NMR (400 MHz, d6-DMSO) δ 10.39 (σ, 1H), 10.03 (σ, 1H), 8.71 (σ, 1H), 7.99-8.01 (m, 2H), 7.82 (s, 1H), 7.43-7.50 (m, 4H), 2.75 (s, 3H).

Workup

  1. customThe solvent and TFA were removed
  2. customby purging with N2
  3. customThe solvent was removed
  4. filtrationfiltered
  5. customThe filtrate was purified by chromatograph in a 8 g AnaLogix column

Sources & evidence

ORD record
ord-7430c6ba19534644b0c8a9a8a0c6ff50
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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