Dimethyl Sulfate → HCID 178480263, compound

HRID 1921301Notes

Reaction equation

HRID 1921301 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:23])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:13]=2[F:22])[N:7]([CH2:24][C@H:25]2[CH2:29][CH2:28][CH2:27][O:26]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].S(OC)(O[CH3:34])(=O)=O>C1(C)C=CC=CC=1>[C:1]([C:5]1[N:6]([CH3:34])[N:7]([CH2:24][C@H:25]2[CH2:29][CH2:28][CH2:27][O:26]2)/[C:8](=[N:10]/[C:11](=[O:23])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[C:13]=2[F:22])/[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 67493097(r)-n-(3-Tert-butyl-1-((tetrahydrofuran-2-yl)methyl)-1h-pyrazol-5-yl)-2-fluoro-3-(trifluoromethyl)benzamide

Product 1

HCID 178480263HCID 178480263, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of Example 6C (400 mg, 0.97 mmol) and dimethyl sulfate (0.37 mL, 3.88 mmol) in toluene (2 mL) was heated in a microwave reactor (300 W, CEM Explorer®) at 150° C. for 1 hour. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (silica gel; solvent A=EtOAc/MeOH/Et3N (90:10:0.5); solvent B=hexane in 10-60% gradient A/B) to yield 331.5 mg (80%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.44 (s, 9H), 1.50-1.67 (m, 1H), 1.75-1.96 (m, 2H), 1.99-2.14 (m, 1H), 3.64-3.84 (m, 2H), 4.12 (s, 3H), 4.18-4.26 (m, 1H), 4.55-4.77 (m, 2H), 6.98 (s, 1H), 7.63 (t, J=7.73 Hz, 1H), 8.00-8.13 (m, 2H); MS (ESI) m/z 428 (M+1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography (silica gel

Sources & evidence

ORD record
ord-820d83cbe3cf4eb0a7ccec5b42c952b0
Source dataset
uspto-grants-2012_05
Patent number
US08173687B2

Reaction notes

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