Hydrochloric Acid → HCID 11475547, compound

HRID 2076444Notes

Reaction equation

HRID 2076444 reaction equation
Cl.[NH2:2][OH:3].[K].[CH3:5][C:6]1([CH3:35])[CH2:15][CH2:14][C:13]([CH3:17])([CH3:16])[C:12]2[CH:11]=[C:10]([C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:34])([F:33])[C:28]([O:30]CC)=O)=[CH:23][CH:22]=3)=[O:19])[CH:9]=[CH:8][C:7]1=2.Cl>CO>[OH:3][NH:2][C:28]([C:27]([F:33])([F:34])[C:24]1[CH:23]=[CH:22][C:21]([NH:20][C:18]([C:10]2[CH:9]=[CH:8][C:7]3[C:6]([CH3:5])([CH3:35])[CH2:15][CH2:14][C:13]([CH3:16])([CH3:17])[C:12]=3[CH:11]=2)=[O:19])=[CH:26][CH:25]=1)=[O:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 5462222PotassiumHCID 23075290HCID 23075290, compound

Product 1

HCID 11475547HCID 11475547, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
45 °C

Procedure

Hydroxylamine hydrochloride (2.34 g, 33.7 mmol) was dissolved in methanol (12 mL) at 45° C. for 10 min in a 50 mL round bottom flask. B) Potassium hydroxyde (2.81 g, 50.0 mmol) was dissolved in methanol (7 mL) at 45° C. for 10 min in 25 mL round bottom flask. The solution B) was added in A) at 45° C. This mixture was stirred at 45° C. for 10 min and cooled to RT. The mixture was filtered and 5 mL of the filtrate were added at RT via syringe to a solution of ethyl 2-(4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido)phenyl)-2,2-difluoroacetate 23 (0.10 g, 0.23 mmol) in methanol (4 mL). This mixture was stirred for 16 h at RT. A solution of HCl 1M was added to about pH=5. The aqueous layer was extracted with ethyl acetate (3×50 mL). The organic layer was dried over MgSO4, filtered and evaporated in vacuo. N-(4-((Hydroxycarbamoyl)difluoromethyl)phenyl)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamide EHT 4996 was obtained (123 mg, 97% yield) as an orange solid.

Workup

  1. temperaturecooled to RT
  2. filtrationThe mixture was filtered
  3. stirringThis mixture was stirred for 16 h at RT
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-b879b3b8605a472e92adc9439c4e6926
Source dataset
uspto-grants-2011_04
Patent number
US07923579B2

Reaction notes

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