Fumaric Acid → HCID 131726719, compound

HRID 969990Notes

Reaction equation

HRID 969990 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:10]1[N:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([N:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=3)=[N:14][CH:15]=1)[CH2:2]2.[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29]>C(OCC)(=O)C.C(O)C>[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29].[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([O:9][C:10]1[N:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([N:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=3)=[N:14][CH:15]=1)[CH2:2]2.[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([O:9][C:10]1[N:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([N:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=3)=[N:14][CH:15]=1)[CH2:2]2

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 11359244HCID 11359244, compound

Product 1

HCID 131726719HCID 131726719, compound

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

The product of Example 16A (130 mg, 0.40 mmol) in ethyl acetate/ethanol (5 mL, 1:1) was treated with fumaric acid (47 mg, 0.4 mmol) at ambient temperature for 10 hours. The title compound was obtained as a solid (101 mg, yield, 63%). 1H NMR (MeOH-d4, 300 MHz) δ 1.74-2.11 (m, 3H), 2.18-2.34 (m, 1H), 2.43-2.51 (m, 1H), 3.00 (s, 6H), 3.08-3.37 (m, 5H), 3.65-3.79 (m, 1H), 5.24-5.33 (m, 1H), 6.67 (s, 1.2H), 6.84 (d, J=8.8 Hz, 2H), 7.80 (d, J=9.2 Hz, 2H), 8.23 (d, J=1.4 Hz, 1H), 8.50 (d, J=1.4 Hz, 1H) ppm. MS (DCl/NH3) m/z 325 (M+H)+. Anal. Calculated for C19H24N4O.0.6C4H4O4.0.3H2O: C, 64.34; H, 6.81; N, 14.03. Found: C, 64.45; H, 7.02; N, 13.86.

Sources & evidence

ORD record
ord-1ab86d9c4b3f415aa24e0ee5849f4bfb
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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