Dimethyl Sulfate → HCID 178480296, compound

HRID 2064500Notes

Reaction equation

HRID 2064500 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[N:7]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].S(OC)(O[CH3:25])(=O)=O>C1(C)C=CC=CC=1>[C:1]([C:5]1[N:6]([CH3:25])[N:7]([CH2:17][CH:18]2[CH2:19][CH2:20]2)/[C:8](=[N:10]/[C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])/[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 59866003n-(3-Tert-butyl-1-(cyclopropylmethyl)-1h-pyrazol-5-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 178480296HCID 178480296, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of Example 9D (11.6 g, 40 mmol) and dimethyl sulfate (20.2 g, 160 mmol) in toluene (10 mL) was heated at 80° C. for 24 hours. The mixture was cooled to room temperature, and concentrated under pressure. The residue was purified by flash chromatography (silica gel, eluted with a gradient of 10-50% hexane in solvent B, solvent B: 10:1:0.5 ethyl acetate:methanol:triethylamine) to afford 8.7 g (72%) of title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.41-0.53 (m, 4H), 1.15-1.27 (m, 1H), 1.38 (s, 9H), 3.98 (s, 3H), 4.20 (d, J=7.12 Hz, 2H), 6.70 (s, 1H); MS (ESI) m/z 304 [M+H]+, 302 [M−H].

Workup

  1. concentrationconcentrated under pressure
  2. customThe residue was purified by flash chromatography (silica gel
  3. washeluted with a gradient of 10-50% hexane in solvent B, solvent B

Sources & evidence

ORD record
ord-c07b8a6e9c4a48ad90e1d5af29552f3c
Source dataset
uspto-grants-2012_10
Patent number
US08288428B2

Reaction notes

Loading…