Fumaric Acid → HCID 131726188, compound

HRID 1372842Notes

Reaction equation

HRID 1372842 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][CH:17]=3)=[CH:12][CH:11]=1)[CH2:2]2.[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29]>CCOC(C)=O.CCO>[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[CH:15]=[CH:14][C:13]([C:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][CH:17]=3)=[CH:12][CH:11]=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[CH:15]=[CH:14][C:13]([C:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][CH:17]=3)=[CH:12][CH:11]=1)[CH2:2]2

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 11255616HCID 11255616, compound

Product 1

HCID 131726188HCID 131726188, compound

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

The product of Example 1B (113 mg, 0.36 mmol) was treated with fumaric acid (46 mg, 0.4 mmol) in EtOAc/EtOH (v. 1:1, 4 mL) at ambient temperature for 10 h. The title compound was obtained as solid (131 mg, yield, 89%). 1H NMR (300 MHz, CD3OD) δ 1.73–2.13 (m, 3H), 2.23–2.37 (m, 1H), 2.43–2.51 (m, 1H), 3.12–3.43 (m, 5H), 3.64–3.76 (m, 1H), 4.77–4.88 (m, 1H), 6.67 (s, 1.4H), 6.99–7.18 (m, 4H), 7.38 (s, 1H), 7.39–7.43 (m, 1H), 7.61 (dt, J=8.8, 2.0 Hz, 2H), 7.80 (d, J=7.8 Hz, 1H) ppm. MS (DCl/NH3): m/z 319 (M+H)+. Anal. Calculated for C21H22N2O.0.85C4H4O4: C, 70.27; H, 6.14; N, 6.72. Found: C, 70.20; H, 6.35; N, 6.88.

Sources & evidence

ORD record
ord-3b0a9aefe9094d6887d5e6ea288830c2
Source dataset
uspto-grants-2007_01
Patent number
US07160876B2

Reaction notes

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