HCID 67327786, compound → HCID 66553675, compound

HRID 1846159Notes

Reaction equation

HRID 1846159 reaction equation
C([O:8][C:9]1[C:10]([CH3:30])=[CH:11][C:12]([NH2:29])=[N:13][C:14]=1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25]COC)C1C=CC=CC=1>CO.Cl.[OH-].[OH-].[Pd+2]>[NH2:29][C:12]1[N:13]=[C:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25])[C:9]([OH:8])=[C:10]([CH3:30])[CH:11]=1

Participants

5

Reactant 1

HCID 67327786HCID 67327786, compound

Product 1

HCID 66553675HCID 66553675, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution containing 113 mg (0.27 mmol) of 5-(benzyloxy)-6-(10-(methoxymethoxy)decyl)-4-methylpyridin-2-amine in 10 mL of methanol were added two drops of concentrated HCl and the mixture was stirred at reflux for 16 h. To the mixture were added 5 mg of 20% palladium hydroxide on carbon (Degussa type E101 NE/N). The reaction mixture was stirred at 23° C. under hydrogen atmosphere for 15 min. The reaction mixture was filtered through celite and the filtrated was concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (10×1 cm). Elution with 17:3 dichloromethane-methanol afforded the expected product as white solid: yield 22 mg (29%); mp: 138-139° C.; silica gel TLC Rf 0.20 (17:3 dichloromethane-methanol); 1H NMR (methanol-d4) δ 1.28-1.35 (m, 12H), 1.48-1.58 (m, 4H), 2.13 (s, 3H), 2.60 (dd, 2H, J=7.6, 7.6 Hz), 3.51 (t, 2H, J=6.8 Hz) and 6.25 (s, 1H); 13C NMR (methanol-d4) δ 15.21, 25.51, 28.78, 29.15, 29.20, 29.22, 29.22, 29.28, 31.49, 32.23, 61.58, 108.39, 139.23, 141.68, 146.88 and 152.45; mass spectrum (APCI+), m/z 281.2231 (M+H) (C16H29N2O2 requires 281.2229).

Workup

  1. temperatureat reflux for 16 h
  2. stirringThe reaction mixture was stirred at 23° C. under hydrogen atmosphere for 15 min
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationthe filtrated was concentrated under diminished pressure
  5. customThe residue was purified by chromatography on a silica gel column (10×1 cm)
  6. washElution with 17:3 dichloromethane-methanol

Sources & evidence

ORD record
ord-2b68a8afc21d4f24a968d081f1a8f177
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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