HCID 70160376, compound → HCID 178432496, compound

HRID 1251086Notes

Reaction equation

HRID 1251086 reaction equation
[F:1][C:2]1([F:56])[CH2:3][CH2:4][N:5]([C:42]([C:44]2[S:48][C:47]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)=[N:46][C:45]=2[CH3:55])=[O:43])[C:6]2[CH:41]=[CH:40][CH:39]=[CH:38][C:7]=2/[C:8]/1=[CH:9]/[C:10]([NH:12][CH2:13][C:14]1[N:15]=[CH:16][N:17](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:18]=1)=[O:11]>C(O)(=O)C>[F:56][C:2]1([F:1])[CH2:3][CH2:4][N:5]([C:42]([C:44]2[S:48][C:47]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)=[N:46][C:45]=2[CH3:55])=[O:43])[C:6]2[CH:41]=[CH:40][CH:39]=[CH:38][C:7]=2/[C:8]/1=[CH:9]/[C:10]([NH:12][CH2:13][C:14]1[N:15]=[CH:16][NH:17][CH:18]=1)=[O:11]

Participants

3

Reactant 1

HCID 70160376HCID 70160376, compound

Product 1

HCID 178432496HCID 178432496, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 190 mg of (Z)-[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]-N-[(1-trityl-1H-imidazol-4-yl)methyl]-acetamide in 20 ml of a 90% aqueous solution of acetic acid was stirred at 60° C. for 1.5 hours. After evaporating the solvent therefrom, ethyl acetate and 3N hydrochloric acid were added to undergo liquid separation. The aqueous layer was neutralized with potassium carbonate and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of NaCl and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was collected by filtration and washed with ethyl acetate to give 110 mg of (Z)-[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]-N-[(1H-imid-azol-4-yl)methyl]acetamide as a colorless powder.

Workup

  1. customAfter evaporating the solvent
  2. additionethyl acetate and 3N hydrochloric acid were added
  3. customliquid separation
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of NaCl
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. filtrationThe residue was collected by filtration
  9. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-3768ed9ff8814aeca30bbb13a1c9561f
Source dataset
uspto-grants-2002_01
Patent number
US06340678B1

Reaction notes

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