Tert-Butylamine → HCID 11683340, compound

HRID 1868597Notes

Reaction equation

HRID 1868597 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([O:25][CH3:26])[CH:24]=1)[C:6]1[O:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[C:10]([O:17][CH2:18][CH:19]1[O:21][CH2:20]1)[CH:9]=2.[C:27]([NH2:31])([CH3:30])([CH3:29])[CH3:28]>CO>[C:27]([NH:31][CH2:20][CH:19]([OH:21])[CH2:18][O:17][C:10]1[CH:9]=[C:8]2[C:13]([C:14](=[O:16])[CH:15]=[C:6]([C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=3)[O:7]2)=[CH:12][CH:11]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 86236608HCID 86236608, compound2×

Product 1

HCID 11683340HCID 11683340, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3′,5′-Dimethoxy-7-(2,3-epoxy-propoxy)-flavone, 32 (500 mg, 1.41 mmol) and tert-butyl amine (0.6 mL, 5.64 mmol) in dry methanol (100 mL) were reacted in a similar manner to that described under 34 to afford 43. Yield 400 mg (66%); mp 145-146° C.; MS (FAB) 428 (M+1); IR (KBr) 3431, 1631; 1H NMR (200 MHz, DMSO-d6) δ 7.93 (d, J=8.8 Hz, 1H), 7.32 (d, J=1.9 Hz, 1H), 7.15 (d, J=2.0 Hz, 2H), 7.08 (dd, J=8.9 Hz, 2.0 Hz, 1H), 6.92 (s, 1H), 6.68 (s, 1H), 4.17-4.01 (m, 3H), 3.82 (s, 6H), 2.77-2.59 (m, 2H), 1.08 (s, 9H). Analysis Calcd for C24H29NO6: C, 67.43; H, 6.84; N, 3.28. Found: C, 67.59; H, 6.73; N, 3.39.

Sources & evidence

ORD record
ord-5c121e095fd549eca25238972e2d2747
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

Loading…