Dimethyl Sulfate → HCID 178490647, compound

HRID 717245Notes

Reaction equation

HRID 717245 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])[N:7]([CH2:22][C@H:23]2[CH2:27][CH2:26][CH2:25][O:24]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].S(OC)(O[CH3:32])(=O)=O>C1(C)C=CC=CC=1>[C:1]([C:5]1[N:6]([CH3:32])[N:7]([CH2:22][C@H:23]2[CH2:27][CH2:26][CH2:25][O:24]2)/[C:8](=[N:10]/[C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])/[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 67544623n-{3-Tert-butyl-1-[(2r)-tetrahydrofuran-2-ylmethyl]-1h-pyrazol-5-yl}-5-chloro-2-methoxybenzamide

Product 1

HCID 178490647HCID 178490647, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of Example 45C (392 mg, 1.0 mmol) and dimethyl sulfate (0.38 mL, 4.0 mmol) in toluene (2 mL) was heated in a microwave at 130° C. for 1 hour. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (silica gel, MeOH/Et3N (90:10) in EtOAc in 10-60% gradient) to yield 223 mg (55%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.44 (s, 9H), 1.51-1.68 (m, 1H), 1.79-1.97 (m, 2H), 2.01-2.18 (m, 1H), 3.62-3.84 (m, 2H), 3.92 (s, 3H), 4.07-4.12 (s, 3H), 4.14-4.26 (m, 1H), 4.50-4.63 (m, 1H), 4.65-4.79 (m, 1H), 6.92-7.02 (m, 1H), 7.31 (d, J=8.82 Hz, 1H), 7.63-7.75 (m, 2H); MS (ESI) m/z 406 [M+H]+, 404 [M−H].

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography (silica gel, MeOH/Et3N (90:10) in EtOAc in 10-60% gradient)

Sources & evidence

ORD record
ord-e3e46ff666694fffbafd41f4e16bd997
Source dataset
uspto-grants-2015_11
Patent number
US09193713B2

Reaction notes

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