HCID 11699738, compound → HCID 11552747, compound

HRID 1868603Notes

Reaction equation

HRID 1868603 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:32]=[C:33]([O:35]CC2C=CC=CC=2)[CH:34]=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]=[C:33]([OH:35])[CH:34]=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]([CH3:29])[CH3:30])[CH:15]=2

Participants

4

Reactant 1

HCID 11699738HCID 11699738, compound2×

Product 1

HCID 11552747HCID 11552747, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3′,5′-Dibenzyloxy-7-(2-hydroxy-3-iso-propylamino-propoxy)-flavone, 35 (1.2 g, 2.12 mmol) was debenzylated in dry methanol (40 mL) with 10% Pd/C (30 mg) under hydrogen atmosphere as described for 48 to provide 49. Yield 800 mg (98%); mp 185° C. (decomposes); MS (FAB) 386 (M++1); IR (KBr) 3244, 1623; 1H NMR (200 MHz, DMSO-d6) δ 9.85 (s, 2H), 7.72 (d, J=8.8 Hz, 1H), 7.06 (d, J=1.7 Hz, 1H), 6.87 (dd, J=8.8 Hz, 1.9 Hz, 1H), 6.66 (d, J=1.7 Hz, 2H), 6.45 (s, 1H), 6.29 (s, 1H), 4.00-3.97 (m, 3H), 3.13-3.03 (m, 1H), 2.94-2.75 (m, 2H), 1.24 (d, J=5.7 Hz, 6H); 13C NMR δ 176.7, 163.3, 163.1, 159.3, 157.7, 133.2, 126.6, 117.6, 115.4, 106.9, 106.3, 104.6, 101.9, 70.9, 65.3, 50.3, 46.9, 19.0, 18.6. Analysis Calcd for C21H23NO6: C, 65.44; H, 6.02; N, 3.63. Found: C, 66.26; H, 6.18; N, 3.44.

Sources & evidence

ORD record
ord-9d3d7c90913e4f82a8aadd47bc6d22e2
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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