Hydrochloric Acid → HCID 57531451, compound

HRID 1091931Notes

Reaction equation

HRID 1091931 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[N:16]=[C:15]([N:17]2[CH2:26][CH2:25][C:20]3(OCC[O:21]3)[CH2:19][CH2:18]2)[C:14]([CH2:27][N:28]([CH3:39])[C@@H:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32][CH2:31][CH2:30]2)=[C:13]([CH3:40])[N:12]=1)[CH3:2].Cl.[OH-].[Na+]>CCOC(C)=O>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[N:16]=[C:15]([N:17]2[CH2:26][CH2:25][C:20](=[O:21])[CH2:19][CH2:18]2)[C:14]([CH2:27][N:28]([CH3:39])[C@@H:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32][CH2:31][CH2:30]2)=[C:13]([CH3:40])[N:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57531473HCID 57531473, compound

Product 1

HCID 57531451HCID 57531451, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a flask containing [2-(2,6-diethyl-phenyl)-4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-6-methyl-pyrimidin-5-ylmethyl]-methyl-(1S)-(1,2,3,4-tetrahydro-naphthalen-1-yl)amine (80 mg, 0.148 mmol) is added HCl (3 M, 20 mL) and the reaction is heated at 60° C. for 4 h. Once cool, the reaction is basified with NaOH (1 N, 100 mL)) and EtOAc (100 mL) is added to extract the product. The organic layer is washed with water (100 mL), brine (100 mL) and dried over Na2SO4. Filtration, concentration and vacuum drying yields the title compound as a colorless gum. [mass expected (496.69); mass found (496.32)].

Workup

  1. temperatureOnce cool
  2. additionis added
  3. extractionto extract the product
  4. washThe organic layer is washed with water (100 mL), brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationFiltration, concentration and vacuum
  7. customdrying

Sources & evidence

ORD record
ord-c889f8d83f8a4d9c954cab59613edac6
Source dataset
uspto-grants-2012_03
Patent number
US08129395B2

Reaction notes

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