2-Methoxyethylamine → N-(3-(4-Chloro-1-methyl-1H-pyrazol-5-yl)-4-(2-(2-methoxyethylamino)-2-oxoethoxy)phenyl)-3-(trifluoromethyl)benzamide

HRID 1685675Notes

Reaction equation

HRID 1685675 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:31])[C:6]=1[C:7]1[CH:17]=[C:16]([NH:18][C:19](=[O:30])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[CH:15]=[CH:14][C:8]=1[O:9][CH2:10][C:11](O)=[O:12].C(N(CC)C(C)C)(C)C.[CH3:41][O:42][CH2:43][CH2:44][NH2:45]>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:31])[C:6]=1[C:7]1[CH:17]=[C:16]([NH:18][C:19](=[O:30])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=2)[CH:15]=[CH:14][C:8]=1[O:9][CH2:10][C:11]([NH:45][CH2:44][CH2:43][O:42][CH3:41])=[O:12]

Participants

6

Reactant 3

HCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 672652962-(2-(4-Chloro-1-methyl-1H-pyrazol-5-yl)-4-(3-(trifluoromethyl)benzamido)phenoxy)acetic Acid

Product 1

HCID 57786635N-(3-(4-Chloro-1-methyl-1H-pyrazol-5-yl)-4-(2-(2-methoxyethylamino)-2-oxoethoxy)phenyl)-3-(trifluoromethyl)benzamideYield 85.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(2-(4-chloro-1-methyl-1H-pyrazol-5-yl)-4-(3-(trifluoromethyl)benzamido)phenoxy)acetic acid (0.060 g, 0.13 mmol) and N,N-diisopropylethylamine (0.034 g, 0.26 mmol) in dichloromethane (1.3 mL) was added BTU (0.075 g, 0.20 mmol) followed by 2-methoxyethylamine (0.015 g, 0.2 mmol). After 1.5 hours the reaction was diluted with ethyl acetate, washed with water, 1 M HCl (×3) and brine, dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography (1:1-1:0 EtOAc/hexane) to give a white solid (57.0 mg, 84%). LCMS m/z (%)=511 (M+H, 35Cl, 100), 513 (M+H, 37Cl, 30). 1H NMR (400 MHz, CDCl3) δ 3.35 (s, 3H) 3.39-3.52 (m, 4H) 3.78 (s, 3H) 4.52 (s, 2H) 6.60 (br. s., 1H) 7.02 (d, J=9.09 Hz, 1H) 7.55 (s, 1H) 7.63-7.67 (m, 2H) 7.74 (dd, J=8.97, 2.91 Hz, 1H) 7.84 (d, J=6.82 Hz, 1H) 7.92 (s, 1H) 8.08 (d, J=6.57 Hz, 1H) 8.14 (s, 1H).

Workup

  1. washwashed with water, 1 M HCl (×3) and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (1:1-1:0 EtOAc/hexane)

Sources & evidence

ORD record
ord-7051a585c973480da0244821338ecc7b
Source dataset
uspto-grants-2012_04
Patent number
US08148418B2

Reaction notes

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