Methanol → HCID 178480296, compound

HRID 883022Notes

Reaction equation

HRID 883022 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.C(OCC)(=O)C.CO>C1(C)C=CC=CC=1.C(N(CC)CC)C>[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

7

Reactant 4

HCID 887MethanolHCID 6497Dimethyl SulfateHCID 8857Ethyl AcetateHCID 59866003n-(3-Tert-butyl-1-(cyclopropylmethyl)-1h-pyrazol-5-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 178480296HCID 178480296, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of Example 1D (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. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, eluted with a gradient of 15-100% hexane in solvent B, solvent B: 10:1:0.5 ethyl acetate:methanol:triethylamine) to afford the title compound (8.7 g, 72% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.41-0.53 (m, 4 H), 1.15-1.27 (m, 1 H), 1.38 (s, 9 H), 3.98 (s, 3 H), 4.20 (d, J=7.12 Hz, 2 H), 6.70 (s, 1 H); MS (ESI) m/z 304 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography
  3. washeluted with a gradient of 15-100% hexane in solvent B, solvent B

Sources & evidence

ORD record
ord-c71fc4c62e31461ba9cb7dd824e7cb9b
Source dataset
uspto-grants-2012_08
Patent number
US08236822B2

Reaction notes

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