HCID 11613861, compound → HCID 11639597, compound

HRID 1868605Notes

Reaction equation

HRID 1868605 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:32]=[CH:33][C:34]=1[O:35]CC1C=CC=CC=1)[C:12]1[O:13][C:14]2[C:19]([C:20](=[O:22])[CH:21]=1)=[CH:18][CH:17]=[C:16]([O:23][CH2:24][CH:25]([OH:31])[CH2:26][NH:27][CH:28]([CH3:30])[CH3:29])[CH:15]=2)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:32]=[CH:33][C:34]=1[OH:35])[C:12]1[O:13][C:14]2[C:19]([C:20](=[O:22])[CH:21]=1)=[CH:18][CH:17]=[C:16]([O:23][CH2:24][CH:25]([OH:31])[CH2:26][NH:27][CH:28]([CH3:29])[CH3:30])[CH:15]=2

Participants

4

Reactant 1

HCID 11613861HCID 11613861, compound2×

Product 1

HCID 11639597HCID 11639597, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3′,4′-Dibenzyloxy-7-(2-hydroxy-3-iso-propylamino-propoxy)-flavone, 38 (1.0 g, 1.77 mmol) was debenzylated in dry methanol (40 mL) with 10% Pd/C (30 mg) under hydrogen atmosphere as described for 48 to provide 51. Yield 600 mg (88%); mp 187° C. (decomposes); MS (FAB) 386 (M++1); IR (KBr) 3425, 1624; 1H NMR (200 MHz, DMSO-d6) δ 7.96 (d, J=7.1 Hz, 1H), 7.47 (s, 1H), 7.45 (d, J=8.2 Hz, 1H), 7.30 (s, 1H), 7.10 (d, J=8.1 Hz, 1H), 6.95 (d, J=7.6 Hz, 1H), 6.68 (s, 1H), 4.23-4.18 (m, 3H), 3.21-3.18 (m, 3H), 1.27 (d, J=6.2 Hz, 6H). Analysis Calcd for C21H23NO6: C, 65.44; H, 6.02; N, 3.63. Found: C, 65.37; H, 6.18; N, 3.47.

Sources & evidence

ORD record
ord-551e525ebfc64277988f4cbdf8d9156d
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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