Methanol → HCID 178481936, compound

HRID 510452Notes

Reaction equation

HRID 510452 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[C:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=2[Cl:21])=[C:11]([OH:22])[NH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:24]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[C:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=2[Cl:21])=[C:11]([OH:22])[N:10]([CH3:24])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 178453009HCID 178453009, compound

Product 1

HCID 178481936HCID 178481936, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl(4-(2,3-dichlorobenzyl)-5-hydroxy-1H-pyrazol-3-yl)carbamate (160 mg, 0.447 mmol), triphenylphosphine (128 mg, 0.491 mol) and methanol (16 mg, 0.491 mol) in anhydrous THF (25 mL), a solution of DIAD (99 mg, 0.491 mmol) in anhydrous THF (2 mL) was added dropwise at 0° C. with stirring. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated. The resulting residue was purified by silica gel chromatography eluted with PE:EA=2:1 to provide the titled compound (50 mg, 30%), as a white solid; LC/MS: MS (ES+) m/e 372 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 1.56 (s, 9H), 3.05 (s, 3H), 3.52 (s, 2H), 7.00 (d, J=7.8 Hz, 1H), 7.11 (s, 2H), 7.25 (t, J=7.8 Hz, 1H), 7.46 (d, J=7.8 Hz, 1H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 h
  2. concentrationThe reaction mixture was concentrated
  3. customThe resulting residue was purified by silica gel chromatography
  4. washeluted with PE

Sources & evidence

ORD record
ord-bed449281fe144268929e0562939d789
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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