Triethylamine → HCID 59489563, compound

HRID 1879206Notes

Reaction equation

HRID 1879206 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]([C:11]2[S:15][C:14]([C:16]3[CH:20]=[CH:19][N:18]([CH2:21][CH2:22][NH2:23])[N:17]=3)=[N:13][C:12]=2[CH3:24])=[O:10])[CH:2]=1.[F:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1.C(N(CC)CC)C>C(Cl)Cl.O.[Cl-].[Na+].O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]([C:11]2[S:15][C:14]([C:16]3[CH:20]=[CH:19][N:18]([CH2:21][CH2:22][NH:23][C:30](=[O:31])[C:29]4[CH:33]=[CH:34][C:26]([F:25])=[CH:27][CH:28]=4)[N:17]=3)=[N:13][C:12]=2[CH3:24])=[O:10])[CH:2]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 86645561HCID 86645561, compound

Product 1

HCID 59489563HCID 59489563, compoundYield 415.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2-[1-(2-amino-ethyl)-1H-pyrazol-3-yl]-4-methyl-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)-amide (0.1 g, 0.29 mmol) in methylene chloride (5 mL) was added 4-fluoro-benzoyl chloride (0.07 mL, 0.44 mmol) and triethyl amine (0.08 mL, 0.58 mmol). The reaction mixture was stirred under nitrogen at room temperature for 16 hr. The reaction mixture was diluted with methylene chloride (50 mL), water (100 mL) and brine (100 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by preparative thin layer chromatography over silica gel (hexanes:ethyl acetate, 1:1) to provide 2-{1-[2-(4-fluoro-benzoylamino)-ethyl]-1H-pyrazol-3-yl}-4-methyl-thiazole-5-carboxylic acid (pyridin-3-ylmethyl)-amide as a white solid (0.56 g, 43%). 1H NMR (400 MHz, CDCl3) δ 8.63 (bs, 1H), 8.57 (d, J=4 Hz, 1H), 7.70-7.81 (m, 3H), 7.46 (d, J=2 Hz, 1H), 7.29-7.33 (m, 1H), 7.09 (t, J=8 Hz, 2H), 6.84 (d, J=2 Hz, 1H), 6.84-6.88 (m, 1H), 6.10-6.15 (bm, 1H), 4.65 (d, J=4 Hz, 2H), 4.42 (bt, J=5 Hz, 2H), 3.89-3.97 (m, 2H), 2.75 (s, 3H); MS (M+H)+=464.8; Rt=1.04 min; HRMS (M+H)+=465.15.

Workup

  1. dry with materialThe organic phase was dried (Na2SO4)
  2. customevaporated
  3. customThe residue was purified by preparative thin layer chromatography over silica gel (hexanes:ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-18d21da4ce8d44f6b45e3d7b6cdcf72c
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

Loading…