Ammonia → HCID 22049682, compound

HRID 1830872Notes

Reaction equation

HRID 1830872 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[C:9]1[S:10][CH:11]=[C:12]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=2)[N:13]=1.C(Cl)(=O)C(Cl)=O.[NH3:31]>O1CCCC1.CN(C)C=O>[F:24][C:2]([F:1])([F:23])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[C:9]1[S:10][CH:11]=[C:12]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([NH2:31])=[O:20])=[CH:16][CH:15]=2)[N:13]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 22049684HCID 22049684, compound

Product 1

HCID 22049682HCID 22049682, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound (162) (0.45 g, 1.29 mmol) in tetrahydrofuran (12 ml) were added oxalyl chloride (0.17 ml, 2.59 mmol) and dimethylformamide (3 drops) under ice-cooling, and the mixture was stirred at room temperature for one hr. To this reaction mixture was added 28% aqueous ammonia (1.00 ml, 16.44 mmol) and the mixture was stirred at room temperature for one hr. and partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate. The aqueous layer was extracted with ethyl acetate. The extracts were combined, washed with brine and dried (MgSO4). The solvent was evaporated under reduced pressure. The obtained residue was crystallized from ethanol-ethyl acetate to give white crystals (0.45 g, quant.).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for one hr
  3. customand partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated under reduced pressure
  8. customThe obtained residue was crystallized from ethanol-ethyl acetate
  9. customto give white crystals (0.45 g, quant.)

Sources & evidence

ORD record
ord-8d3635c6c2114cd4897039dbc96f27a8
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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