1,2-Ethanediamine, N1-phenyl- → HCID 10164451, compound

HRID 2085476Notes

Reaction equation

HRID 2085476 reaction equation
C1([O:7][C:8](=O)[C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[S:17][C:18]([C:22](=[O:31])[C:23]4[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=4[F:30])=[C:19]([NH2:21])[N:20]=3)=[CH:11][C:10]=2[OH:32])C=CC=CC=1.[C:34]1([NH:40][CH2:41][CH2:42][NH2:43])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C=O)C>[NH2:21][C:19]1[N:20]=[C:16]([NH:15][C:12]2[CH:13]=[CH:14][C:9]([C:8]([NH:43][CH2:42][CH2:41][NH:40][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:7])=[C:10]([OH:32])[CH:11]=2)[S:17][C:18]=1[C:22](=[O:31])[C:23]1[C:24]([F:30])=[CH:25][CH:26]=[CH:27][C:28]=1[F:29]

Participants

4

Reactant 2

HCID 742701,2-Ethanediamine, N1-phenyl-HCID 21307325HCID 21307325, compound

Product 1

HCID 10164451HCID 10164451, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[4-amino-5-(2,6-difluoro-benzoyl)-thiazol-2-ylamino]-2-hydroxy-benzoic acid phenyl ester (16) and N-phenyl-ethylene-diamine (5 eq) in DMF was heated at 70° C. for 1 hour. DMF was removed under reduced pressure and the solution of resultant residue in ethyl acetate was washed with saturated aqueous NaHCO3 solution, brine, dried with MgSO4, filtered and concentrated. The product was purified by HPLC.

Workup

  1. customDMF was removed under reduced pressure
  2. washthe solution of resultant residue in ethyl acetate was washed with saturated aqueous NaHCO3 solution, brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by HPLC

Sources & evidence

ORD record
ord-a758cbea85894321ac38fc31ae38d97d
Source dataset
uspto-grants-2004_04
Patent number
US06720346B2

Reaction notes

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