Ethylamine hydrochloride → HCID 11283602, compound

HRID 494368Notes

Reaction equation

HRID 494368 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8](O)=[O:9])[C:5]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[N:24]=[C:25]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[O:26][C:27]=3[CH3:28])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[N:4]1)[CH3:2].[CH3:35][CH2:36][N:37]=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.Cl.C(N)C>C(Cl)Cl.C(OCC)(=O)C>[CH2:36]([NH:37][C:8]([C:6]1[C:5]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[N:24]=[C:25]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[O:26][C:27]=3[CH3:28])=[CH:17][CH:16]=2)(=[O:13])=[O:14])=[N:4][N:3]([CH2:1][CH3:2])[CH:7]=1)=[O:9])[CH3:35]

Participants

7

Reactant 4

HCID 11198Ethylamine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11386125HCID 11386125, compound

Product 1

HCID 11283602HCID 11283602, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the title compound of Example 3 (0.15 g, 0.31 mmol), EDCl (0.12 g, 0.62 mmol), 1-hydroxybenzotriazole (0.42 g, 0.31 mmol) and TEA (0.2 g, 1.5 mmol) in DCM, is added ethylamine hydrochloride (0.5 g, 0.62 mmol) at RT. The reaction mixture is stirred for 16 h. The reaction mixture is diluted with ethyl acetate, washed with 1N hydrochloric acid, water and brine. The organic filtrate is concentrated, the crude is chromatographed using 25% ethyl acetate in hexanes to provide 1-ethyl-3-{4-[5-methyl-2-phenyl-oxazol-4-ylmethoxy]-benzenesulfonylamino}-1H-pyrazole-4-carboxylic acid ethyl amide as a crystalline solid: MS [m/z] 508.1 [M-1]−.

Workup

  1. washwashed with 1N hydrochloric acid, water and brine
  2. concentrationThe organic filtrate is concentrated
  3. customthe crude is chromatographed

Sources & evidence

ORD record
ord-766a2f6b0eb6498bb46acdb735d0e1d4
Source dataset
uspto-grants-2009_05
Patent number
US07538135B2

Reaction notes

Loading…