Ammonia → 2-{2-{[2-(4-Tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}-pentanamide

HRID 1604697Notes

Reaction equation

HRID 1604697 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:34]=[CH:33][CH:32]=[CH:31][C:22]=4[O:23][CH:24]([CH2:28][CH2:29][CH3:30])[C:25]([OH:27])=O)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].O[N:36]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.N>CN(C)C=O.O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:34]=[CH:33][CH:32]=[CH:31][C:22]=4[O:23][CH:24]([CH2:28][CH2:29][CH3:30])[C:25]([NH2:36])=[O:27])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 196038262-{2-{[2-(4-Tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}pentanoic acid

Product 1

HCID 196038242-{2-{[2-(4-Tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}-pentanamideYield 102.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-{2-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}pentanoic acid (500 mg) and 1-hydroxybenzotriazole (141 mg) in dimethylformamide (5 ml) was added N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride (200 mg) at room temperature. The solution was stirred for an hour at the same temperature and was ice-cooled. Then concentrated solution of ammonia (0.3 ml) was added into the solution and the resulting mixture was stirred further for an hour. The mixture was diluted with water and was extracted with ethyl acetate. The organic layer was separated and was washed successively with sodium hydrogen carbonate solution and brine, and was dried over magnesium sulfate. Concentration gave 2-{2-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}-pentanamide (510 mg).

Workup

  1. temperaturecooled
  2. stirringthe resulting mixture was stirred further for an hour
  3. extractionwas extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwas washed successively with sodium hydrogen carbonate solution and brine
  6. dry with materialwas dried over magnesium sulfate
  7. concentrationConcentration

Sources & evidence

ORD record
ord-642033a6aa494f2d9fe0d471cc6bb386
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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