HCID 86718011, compound → HCID 86718012, compound

HRID 1500474Notes

Reaction equation

HRID 1500474 reaction equation
[CH3:1][C@@H:2]1[CH2:6][C:5]2[C:7]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[C:8]([CH3:12])[CH:9]=[C:10]([NH2:11])[C:4]=2[O:3]1>CC(O)=O.O=[Pt]=O>[CH3:1][C@@H:2]1[CH2:6][C:5]2[C:7]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[C:8]([CH3:12])[CH:9]=[C:10]([NH2:11])[C:4]=2[O:3]1

Participants

4

Reactant 1

HCID 86718011HCID 86718011, compound

Product 1

HCID 86718012HCID 86718012, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

[The mixture of (R)-2,5-dimethyl-4-(pyridin-4-yl)-2,3-dihydrobenzofuran-7-amine (3h) (0.60 g, 2.4 mmol), PtO2 (240 mg, 35%) and TEA (0.38 mL, 4.9 mmol) in HOAc (40 mL) was introduced H2 and stirred for 24 h at ambient temperature (88 psi). The mixture was filtered, concentrated, and diluted with EtOAc (50 mL). A solution of ammonium hydroxide was added until pH=10, then extracted with EtOAc (150 mL), washed with water, brine, dried and concentrated to give the title compound (3i) as a yellow oil. MS-ESI (m/z): 247 (M+1)+.

Workup

  1. additionwas introduced H2
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. additiondiluted with EtOAc (50 mL)
  5. additionA solution of ammonium hydroxide was added until pH=10
  6. extractionextracted with EtOAc (150 mL)
  7. washwashed with water, brine
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0d0e6b3ad99e4d9ea7c3afa1748731fb
Source dataset
uspto-grants-2015_12
Patent number
US09206166B2

Reaction notes

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