4-Phenoxybenzoic acid → HCID 68521959, compound

HRID 2247738Notes

Reaction equation

HRID 2247738 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH2:39]([C:41]1[CH:42]=[C:43]([C:54](=[N:56]O)[NH2:55])[S:44][C:45]=1[CH2:46][O:47][CH:48]1[CH2:53][CH2:52][CH2:51][CH2:50][O:49]1)[CH3:40].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:39]([C:41]1[CH:42]=[C:43]([C:54]2[N:56]=[C:12]([C:11]3[CH:10]=[CH:9][C:8]([O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:16][CH:15]=3)[O:14][N:55]=2)[S:44][C:45]=1[CH2:46][O:47][CH:48]1[CH2:53][CH2:52][CH2:51][CH2:50][O:49]1)[CH3:40]

Participants

7

Reactant 5

HCID 751824-Phenoxybenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724141Tetrabutylammonium FluorideHCID 86620224HCID 86620224, compound

Product 1

HCID 68521959HCID 68521959, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude product of the title compound was synthesized by conducting the similar reaction to that mentioned in Example 5 (5a) using 4-phenoxybenzoic acid (0.16 g, 0.73 mmol), 1-hydroxybenzotriazole (0.12 g, 0.76 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.15 g, 0.76 mmol), 4-ethyl-N′-hydroxy-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]thiophene-2-carboximidamide (0.17 g, 0.69 mmol) that was obtained in Example 22 (22d) and tetrabutylammonium fluoride (a 1.0 M solution in tetrahydrofuran, 14 ml, 1.4 mmol). Subsequently, the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (0:10 to 2:8) as the eluent to afford the title compound (0.25 g) in a yield of 78% as a colourless oily product.

Workup

  1. customthe similar reaction to

Sources & evidence

ORD record
ord-2ce976adf07b40d1879e56f89a27df2b
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

Loading…