Ammonia → 5-(4-Methoxyphenyl)-2-(thiophen-2-yl)oxazole-4-carboxamide

HRID 389727Notes

Reaction equation

HRID 389727 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)=[N:11][C:10]=2[C:19]([OH:21])=O)=[CH:5][CH:4]=1.O.OC1C2N=N[NH:29]C=2C=CC=1.N.O1CCOCC1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C=O)C.CN(C=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)=[N:11][C:10]=2[C:19]([NH2:29])=[O:21])=[CH:5][CH:4]=1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 292814635-(4-Methoxyphenyl)-2-(thiophen-2-yl)oxazole-4-carboxylic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 595875645-(4-Methoxyphenyl)-2-(thiophen-2-yl)oxazole-4-carboxamideYield 15%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a solution of 5-(4-methoxyphenyl)-2-(thiophen-2-yl)oxazole-4-carboxylic acid in DCM (2 mL) and DMF (1 mL) was added hydroxybenzotriazole monohydrate (0.022 g, 0.14 mmol) followed by 0.5M ammonia in dioxane (1.3 mL, 0.65 mmol). A solution of 1-(3-(dimethylamino)propyl)-3-ethyl-carbodiimide hydrochloride (0.078 g, 0.41 mmol) in DMF/DCM (4:1, 0.5 mL) was added and the reaction stirred at room temperature overnight. The solvents were removed in vacuo and the residue was purified by preparative HPLC to afford 5-(4-methoxyphenyl)-2-(thiophen-2-yl)oxazole-4-carboxamide (0.0128 g, 0.04 mmol, 15%) as a white solid. 1H NMR (CDCl3) δ 3.85 (3H, s), 5.53 (1H, br. s), 7.00 (2H, d), 7.16 (1H, dd), 7.17 (1H, br. s), 7.48 (1H, dd), 7.74 (1H, dd), 8.32 (2H, d). LCMS (2) Rt: 2.90 min; m/z (ES+) 301.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-ab1bd139a327461494b1070db078659e
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

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