Dimethyl Sulfate → HCID 178480296, compound

HRID 536710Notes

Reaction equation

HRID 536710 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 54.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of Example 27D (11.6 g, 40 mmol) and dimethyl sulfate (20.2 g, 160 mmol) in toluene (10 mL) was heated in a microwave at 150° C. for 30 min. The mixture was concentrated and purified by flash chromatography (silica gel, MeOH/Et3N (10:1)/EtOAc in 10-60% gradient) to yield 6.6 g (54.4%) of the title compound. 1H NMR (300 MHz, DMSO-d6) 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. concentrationThe mixture was concentrated
  2. custompurified by flash chromatography (silica gel, MeOH/Et3N (10:1)/EtOAc in 10-60% gradient)

Sources & evidence

ORD record
ord-5bf49e7709fd4a259e9d50ba58d0656f
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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