Ammonia → HCID 19603818, compound

HRID 1604696Notes

Reaction equation

HRID 1604696 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:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:22]=4OC(C)C(O)=O)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH:35]N1C2C=CC=CC=2N=N1.Cl.C(N=C=NC[CH2:52][CH2:53]N(C)C)C.N.C[N:59](C)[CH:60]=[O:61]>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:22]=[CH:29][CH:30]=[C:31]([O:33][CH3:34])[C:32]=4[O:35][CH:52]([CH3:53])[C:60]([NH2:59])=[O:61])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19603777HCID 19603777, compound

Product 1

HCID 19603818HCID 19603818, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-{2-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}-4-methoxyphenoxy}propanoic acid (1.57 g) and 1-hydroxybenzotriazole (0.439 g) in dimethylformamide (20 ml) was added 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (0.63 g) at room temperature. The solution was stirred for an hour at the same temperature and was ice-cooled. Then concentrated solution of ammonia (1.1 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. After concentration, the residue (1.50 g) was crystallized with diisopropyl ether, filtered, and dried under reduced pressure to give 2-{2-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}-6-methoxyphenoxy}propionamide (1.37 g).

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. concentrationAfter concentration
  8. customthe residue (1.50 g) was crystallized with diisopropyl ether
  9. filtrationfiltered
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-fe244c5c9f194126ba59077aa638b0ec
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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