HCID 11534361, compound → HCID 11718263, compound

HRID 1868606Notes

Reaction equation

HRID 1868606 reaction equation
[C:1]([NH:5][CH2:6][CH:7]([OH:43])[CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[O:16][C:15]([C:20]1[CH:25]=[CH:24][C:23]([O:26]CC3C=CC=CC=3)=[C:22]([O:34]CC3C=CC=CC=3)[CH:21]=1)=[CH:14][C:13]2=[O:42])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([NH:5][CH2:6][CH:7]([OH:43])[CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[O:16][C:15]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([OH:34])[CH:21]=1)=[CH:14][C:13]2=[O:42])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 11534361HCID 11534361, compound2×

Product 1

HCID 11718263HCID 11718263, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6-(3-tert-Butylamino-2-hydroxy-propoxy)-3′,4′-dibenzyloxy-flavone, 39 (1.16 g, 2 mmol) was debenzylated in dry methanol (40 mL) with 10% Pd/C (30 mg) under hydrogen atmosphere as described for 48 to provide 52. Yield 740 mg (93%); mp 193° C. (decomposes); MS (FAB) 400 (M++1); IR (KBr) 3399, 1616; 1H NMR (200 MHz, DMSO-d6) δ 7.93 (s, 1H), 7.55 (d, J=9.5 Hz, 1H), 7.53 (s, 1H), 7.39 (d, J=9.8 Hz, 1H), 7.34 (d, J=8.5 Hz, 1H), 6.93 (d, J=8.0 Hz, 1H), 6.62 (s, 1H), 4.41-4.12 (m, 3H), 3.07-2.93 (m, 2H), 1.33 (s, 9H). Analysis. Calcd for C22H25NO6: C, 66.15; H, 6.31; N, 3.51. Found: C, 66.26; H, 6.47; N, 3.61.

Sources & evidence

ORD record
ord-6414af7ba2b7455381268703cd6a98d0
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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