Dimethylformamide → HCID 67255853, compound

HRID 2426966Notes

Reaction equation

HRID 2426966 reaction equation
OC1C(O)=CC=CC=1C([O:6][CH:7]([C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=1[F:33])[C:8]([C:10]1[CH:15]=[CH:14][C:13](=[O:16])[N:12]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([Cl:24])=[CH:19][C:18]=2[CH3:25])[CH:11]=1)=O)=O.C[N:40](C)[CH:41]=[O:42].[C:44]([O-:47])(=O)[CH3:45].[NH4+].[OH-:49].[Na+]>C(O)(=O)C>[Cl:24][C:20]1[CH:21]=[C:22]([CH3:23])[C:17]([N:12]2[C:13](=[O:16])[CH:14]=[CH:15][C:10]([CH:8]([NH:40][C:41](=[O:42])[C:7]3[CH:8]=[CH:10][CH:45]=[C:44]([OH:47])[C:26]=3[OH:49])[C:7]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=3[F:33])=[O:6])=[CH:11]2)=[C:18]([CH3:25])[CH:19]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 67256120HCID 67256120, compound

Product 1

HCID 67255853HCID 67255853, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a mixed solution of the compound prepared in Example 45 (413 mg) in acetic acid (7.6 mL)-N,N-dimethylformamide (7.0 mL) was added ammonium acetate (1.18 g) and the mixture was stirred at 100° C. for an hour. The reaction mixture was poured into 5N aqueous solution of sodium hydroxide and the mixture was extracted with ethyl acetate. After having made the water layer acidity with 2N hydrochloric acid, the mixture was extracted with ethyl acetate. The organic layer was put together, washed with brine, dried and concentrated. The obtained residue was purified by preparative medium pressure liquid chromatography W-prep 2XY (column: main column L, inject column M; automatic condition setting: hexane:ethyl acetate=1:1, Rf=0.30, preparative isolation mode GR) to give the title compound having the following physical data.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe obtained residue was purified by preparative medium pressure liquid chromatography W-prep 2XY (column: main column L, inject column M; automatic condition setting: hexane:ethyl acetate=1:1, Rf=0.30, preparative isolation mode GR)

Sources & evidence

ORD record
ord-1c2d291006c1422a8f5d74f5ec4e4647
Source dataset
uspto-grants-2011_06
Patent number
US07968572B2

Reaction notes

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