Sodium Bicarbonate → HCID 70160851, compound

HRID 1251083Notes

Reaction equation

HRID 1251083 reaction equation
[F:1][C:2]1([F:45])[CH2:3][CH2:4][N:5]([C:31]([C:33]2[S:37][C:36]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[N:35][C:34]=2[CH3:44])=[O:32])[C:6]2[CH:30]=[CH:29][CH:28]=[CH:27][C:7]=2/[C:8]/1=[CH:9]/[C:10]([NH:12][CH2:13][CH:14]1[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]1)=[O:11].[ClH:46].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[ClH:46].[ClH:46].[F:45][C:2]1([F:1])[CH2:3][CH2:4][N:5]([C:31]([C:33]2[S:37][C:36]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)=[N:35][C:34]=2[CH3:44])=[O:32])[C:6]2[CH:30]=[CH:29][CH:28]=[CH:27][C:7]=2/[C:8]/1=[CH:9]/[C:10]([NH:12][CH2:13][CH:14]1[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1)=[O:11]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 86757742HCID 86757742, compound

Product 1

HCID 70160851HCID 70160851, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 420 mg of tert-butyl (Z)-{4-[({[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]acetyl}amino)methyl]-piperidino}carboxylate in 6 ml of ethyl acetate was added 660 μl of a 4N HCl/ethyl acetate solution, followed by stirring at room temperature for 1.5 days. To the reaction solution was added a saturated aqueous solution of sodium bicarbonate, 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. The residue was purified by silica gel column chromatography (eluting with methanol) and, after making into a hydrochloride using a 4N HCl/ethyl acetate solution, the salt was collected by filtration and washed with ethyl acetate to give 97 mg of (Z)-[4,4-difluoro-1-(4-methyl-2phenyl -thiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]-N-[(4-piperidyl)methyl]acetamide dihydrochloride as a colorless powder.

Workup

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

Sources & evidence

ORD record
ord-a1de12bc54c64b538a369ed23b2b2d5f
Source dataset
uspto-grants-2002_01
Patent number
US06340678B1

Reaction notes

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