Fumaric Acid → HCID 69432614, compound

HRID 969969Notes

Reaction equation

HRID 969969 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=3)=[CH:12][CH:11]=1)[CH2:2]2.[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27]>C(OCC)(=O)C.CO>[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@@H:3]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=3)=[CH:14][CH:15]=1)[CH2:2]2

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 11266380HCID 11266380, compound

Product 1

HCID 69432614HCID 69432614, compound

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

The product of Example 2B (38 mg, 0.13 mmol) in ethyl acetate/methanol (3 mL, 10:1) was treated with fumaric acid (17 mg, 0.14 mmol) at ambient temperature overnight. The title compound was obtained as a solid (31 mg, yield, 55%): 1H NMR (MeOH-d4, 300 MHz) δ 1.82-2.21 (m, 3H), 2.30-2.42 (m, 1H), 2.55-2.62 (m, 1H), 3.35-3.50 (m, 5H), 3.75-3.82 (m, 1H), 4.95-5.02 (m, 1H), 6.65-6.72 (m, 3H), 6.88 (ddd, J=7.8, 2.7, 1.0 Hz, 1H), 6.92 (t, J=2.0 Hz, 1H), 7.01 (dt, J=8.8, 2.1 Hz, 2H), 7.14 (t, J=7.8 Hz, 1H), 7.53 (dt, J=8.8, 2.5 Hz, 2H) ppm. MS (DCl/NH3) m/z 295 (M+H)+. Anal. Calculated for C19H22N2O.1.19C4H4O4: C, 65.98; H, 6.24; N, 6.48. Found: C, 66.00; H, 6.00; N, 6.38.

Sources & evidence

ORD record
ord-f51a9a0214c7472f9bbc0d299af91c9f
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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