Trifluoroacetic acid → 5-(2-ureidoethoxy)-7-chloro-1-[2-methoxy-4-(2-chloro-benzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

HRID 1291556

Reaction equation

HRID 1291556 reaction equation
[O-:1][C:2]#[N:3].[Na+].FC(F)(F)C(O)=O.[NH2:12][CH2:13][CH2:14][O:15][CH:16]1[C:22]2[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=2[N:20]([C:28](=[O:47])[C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36](=[O:44])[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[Cl:43])=[CH:31][C:30]=2[O:45][CH3:46])[CH2:19][CH2:18][CH2:17]1.C(=O)([O-])O.[Na+]>CN(C)C=O.CCCCCC>[NH:12]([CH2:13][CH2:14][O:15][CH:16]1[C:22]2[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=2[N:20]([C:28](=[O:47])[C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36](=[O:44])[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[Cl:43])=[CH:31][C:30]=2[O:45][CH3:46])[CH2:19][CH2:18][CH2:17]1)[C:2]([NH2:3])=[O:1]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 517096Sodium CyanateHCID 189172105-(2-aminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

Product 1

HCID 189171925-(2-ureidoethoxy)-7-chloro-1-[2-methoxy-4-(2-chloro-benzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepineYield 76%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

0.12 g of sodium cyanate and 0.22 ml of trifluoro-acetic acid were added to a solution of 0.5 g of 5-(2-amino-ethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine dissolved in 15 ml of dry dimethylformamide. The mixture was stirred at 80° C. for 1 hour. After cooling, the reaction mixture was mixed with slight amounts of a saturated aqueous sodium hydrogen-carbonate solution and hexane, followed by extraction with ethyl acetate. The organic layer was water-washed, then dried over magnesium sulfate and subjected to vacuum distillation to remove the solvent. The residue was recrystallized from acetone-n-hexane to obtain 0.41 g (76%) of 5-(2-ureidoethoxy)-7-chloro-1-[2-methoxy-4-(2-chloro-benzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washwashed
  4. dry with materialdried over magnesium sulfate
  5. distillationsubjected to vacuum distillation
  6. customto remove the solvent
  7. customThe residue was recrystallized from acetone-n-hexane

Sources & evidence

ORD record
ord-961c567921b04efbb955b235f960f1dd
Source dataset
uspto-grants-1998_05
Patent number
US05753644

Linked notes

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