Hydrochloric Acid → HCID 70160939, compound

HRID 1251087Notes

Reaction equation

HRID 1251087 reaction equation
[F:1][C:2]1([F:42])[CH2:3][CH2:4][N:5]([C:28]([C:30]2[S:34][C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[N:32][C:31]=2[CH3:41])=[O:29])[C:6]2[CH:27]=[CH:26][CH:25]=[CH:24][C:7]=2/[C:8]/1=[CH:9]/[C:10]([N:12]1[CH2:17][CH2:16][CH:15]([C:18](N(OC)C)=[O:19])[CH2:14][CH2:13]1)=[O:11].[CH3:43][Li].Cl>O1CCCC1.C(OCC)C>[F:1][C:2]1([F:42])[CH2:3][CH2:4][N:5]([C:28]([C:30]2[S:34][C:33]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[N:32][C:31]=2[CH3:41])=[O:29])[C:6]2[CH:27]=[CH:26][CH:25]=[CH:24][C:7]=2/[C:8]/1=[CH:9]/[C:10]([N:12]1[CH2:13][CH2:14][CH:15]([C:18](=[O:19])[CH3:43])[CH2:16][CH2:17]1)=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 88184866HCID 88184866, compoundHCID 178418348HCID 178418348, compound2×

Product 1

HCID 70160939HCID 70160939, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of 140 mg of (Z)-(1-{[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]acetyl}-4-piperidyl)-N-methoxy-N-methylcarboxamide in 10 ml of tetrahydrofuran was added 280 μl of a solution of 1.05N methyl lithium in diethyl ether at −30° C. This was stirred at −30° C. for three hours together while adding 200 μl of the above-mentioned methyl lithium solution thereto every 40 minutes. To the reaction solution was added 1N hydrochloric acid, followed by extracting with ethyl acetate. The organic layer was washed with a saturated aqueous solution of NaCl and dried over anhydrous magnesium sulfate, followed by evaporating the solvent therefrom. The residue was purified by silica gel column chromatography (eluting with chloroform) to give 20 mg of (Z)-4,4-difluoro-5-[2-(4-acetylpiperidino)-2-oxoethylidene]-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepine as a yellow amorphous solid.

Workup

  1. customevery 40 minutes
  2. extractionby extracting with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of NaCl
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customby evaporating the solvent
  6. customThe residue was purified by silica gel column chromatography (eluting with chloroform)

Sources & evidence

ORD record
ord-82e4a3e4d217486fac968a7e654438ee
Source dataset
uspto-grants-2002_01
Patent number
US06340678B1

Reaction notes

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