Fumaric Acid → HCID 69432362, compound

HRID 970003Notes

Reaction equation

HRID 970003 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([O:9][C:10]1[N:15]=[CH:14][C:13]([C:16]3[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=3)[NH2:19])=[CH:12][N: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.C(O)C>[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[N:15]=[CH:14][C:13]([C:16]3[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=3)[NH2:19])=[CH:12][N:11]=1)[CH2:2]2

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 11277880HCID 11277880, compound

Product 1

HCID 69432362HCID 69432362, compound

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

The product of Example 22B (284 mg, 0.96 mmol) in ethyl acetate:ethanol (1:1, 10 mL) was treated with fumaric acid (116 mg, 1.0 mmol) at ambient temperature for 10 hours. The title compound was obtained as a solid (351 mg, yield, 87%). 1H NMR (300 MHz, MeOH-d4) δ 1.78-2.13 (m, 3H), 2.22-2.38 (m, 1H), 2.48-2.55 (m, 1H), 3.12-3.39 (m, 5H), 3.71-3.83 (m, 1H), 5.31-5.39 (m, 1H), 6.67 (s, 1.8H), 6.76 (ddd, J=8.2, 2.1, 1.0 Hz, 1H), 6.90 (ddd, J=7.4, 1.7, 1.0 Hz, 1H) 6.94 (t, J=1.8 Hz, 1H), 7.21 (t, J=7.8 Hz, 1H), 8.79 (s, 2H) ppm. MS (DCl/NH3) m/z 297 (M+H)+. Anal. Calculated for C17H20N4O.1.0C4H4O4.0.25H2O: C, 60.49; H, 5.92; N, 13.44. Found: C, 60.49; H, 5.94; N, 13.35.

Sources & evidence

ORD record
ord-bc3b182a8a4e4836b480255e1e2ff147
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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