Ammonia → HCID 59587587, compound

HRID 389760Notes

Reaction equation

HRID 389760 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12](NC3C=CC=CC=3)=[N:11][C:10]=2[C:21]([OH:23])=O)=[CH:5][CH:4]=1.O.O[N:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2N=N1.Cl.C[N:37](C)CCCN=C=NCC.N.O1CCOCC1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][C:12]([NH:26][C:30]3[CH:29]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:11][C:10]=2[C:21]([NH2:37])=[O:23])=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59587504HCID 59587504, compound

Product 1

HCID 59587587HCID 59587587, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-(4-methoxyphenyl)-2-(phenylamino)oxazole-4-carboxylic acid (0.012 g, 0.039 mmol), 1-hydroxybenzotriazole hydrate (0.009 g, 0.059 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.011 g, 0.057 mmol) in DMF (5 mL) was added a 0.5M ammonia in dioxane solution (0.116 mL, 0.058 mmol) and the resulting mixture stirred at room temperature overnight. The solvent was removed in vacuo and the residue purified by preparative HPLC to afford 5-(4-methoxyphenyl)-2-(phenylamino)oxazole-4-carboxamide (0.0045 g, 0.015 mmol, 38%). 1H NMR (DMSO) δ 3.82 (3H, s), 6.98 (1H, t), 7.04 (2H, d), 7.33 (2H, t), 7.51 (1H, br, s), 7.60 (1H, br, s), 7.73 (2H, d), 8.16 (2H, d), 10.40 (1H, s). LCMS (2) Rt: 2.67 min; m/z (ES+) 310.

Workup

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

Sources & evidence

ORD record
ord-316283b4100049c199afaf018d304b71
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

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