Fumaric Acid → HCID 131727869, compound

HRID 1441443Notes

Reaction equation

HRID 1441443 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[N:15]=[N:14][C:13]([O:16][CH:17]3[CH:22]4[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]4)[CH2:18]3)=[CH:12][CH:11]=2)=[CH:2]1.[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29]>CCOC(C)=O.CO>[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29].[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[N:15]=[N:14][C:13]([O:16][CH:17]3[CH:22]4[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]4)[CH2:18]3)=[CH:12][CH:11]=2)=[CH:2]1.[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[N:15]=[N:14][C:13]([O:16][CH:17]3[CH:22]4[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]4)[CH2:18]3)=[CH:12][CH:11]=2)=[CH:2]1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 11450046HCID 11450046, compound

Product 1

HCID 131727869HCID 131727869, compoundYield 103.7%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

The product of Example 39A (200 mg, 0.63 mmol) was treated with fumaric acid (Aldrich, 73 mg, 0.63 mmol) in EtOAc/MeOH (v.10:1, 10 mL) at ambient temperature overnight to give the title compound (247.3 mg, 100%). 1H NMR (MeOH-D4, 300 MHz) 1.76-1.91 (m, 1H), 1.92-2.14 (m, 2H), 2.22-2.37 (m, 1H), 2.51-2.58 (m, 1H), 3.16-3.39 (m, 5H), 3.82 (ddd, J=14.0, 8.2, 1.9 Hz, 1H), 5.40-5.49 (m, 1H), 6.67 (s, 1H), 7.12-7.26 (m, 3H), 7.42-7.49 (m, 1H), 7.89 (s, 1H), 8.05 (d, J=9.5 Hz, 1H), 8.26-8.32 (m, 1H) ppm. MS (DCI/NH3) m/z 321(M+H)+. Anal. Calculated for C19H20N4O.0.5 C4O4H4.0.35 H2O: C, 65.56; H, 5.95; N, 14.56. Found: C, 65.49; H, 6.21; N, 14.34.

Sources & evidence

ORD record
ord-c193432382824138b869bc71daba2973
Source dataset
uspto-grants-2010_02
Patent number
US07655657B2

Reaction notes

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