HCID 11541536, compound → HCID 11618226, compound

HRID 1868604Notes

Reaction equation

HRID 1868604 reaction equation
[C:1]([NH:5][CH2:6][CH:7]([OH:43])[CH2:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14](=[O:42])[CH:15]=[C:16]([C:20]3[CH:25]=[CH:24][C:23]([O:26]CC4C=CC=CC=4)=[C:22]([O:34]CC4C=CC=CC=4)[CH:21]=3)[O:17]2)=[CH:12][CH:11]=1)([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:19]=[C:18]2[C:13]([C:14](=[O:42])[CH:15]=[C:16]([C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([OH:34])[CH:21]=3)[O:17]2)=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 11541536HCID 11541536, compound2×

Product 1

HCID 11618226HCID 11618226, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

7-(3-tert-Butylamino-2-hydroxy-propoxy)-3′,4′-dibenzyloxy-flavone, 37 (1.4 g, 2.4 mmol) was debenzylated in dry methanol (40 mL) with 10% Pd/C (30 mg) under hydrogen atmosphere as described for 48 to provide 50. Yield 930 mg (97%); mp 165° C. (decomposes); MS (FAB) 400 (M++1); IR (KBr) 3274, 1623; 1H NMR (200 MHz, DMSO-d6) δ 7.95 (d, J=8.8 Hz, 1H), 7.47 (s, 1H), 7.44 (d, J=9.4 Hz, 1H), 7.29 (s, 1H), 7.10 (d, J=8.8 Hz, 1H), 6.95 (d, J=8.1 Hz, 1H), 6.68 (s, 1H), 4.28-4.19 (m, 3H), 3.18-3.14 (m, 1H), 2.97-2.94 (m, 1H), 1.34 (s, 9H). Analysis Calcd for C22H25NO6: C, 66.15; H, 6.31; N, 3.51. Found: C, 66.26; H, 6.27; N, 3.27.

Sources & evidence

ORD record
ord-719f90d9c78142b6a96d19e0e627158e
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

Loading…