Fumaric Acid → HCID 67069975, compound

HRID 1441435Notes

Reaction equation

HRID 1441435 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[N:15]=[N:14][C:13]([O:16][C@H:17]4[CH:22]5[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]5)[CH2:18]4)=[CH:12][CH:11]=3)=[CH:7][CH:8]=2)[CH:3]=[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][C:6]([C:10]3[N:15]=[N:14][C:13]([O:16][C@H:17]4[CH:22]5[CH2:21][CH2:20][N:19]([CH2:24][CH2:23]5)[CH2:18]4)=[CH:12][CH:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 11472679HCID 11472679, compound

Product 1

HCID 67069975HCID 67069975, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

The product of Example 30B (200 mg, 0.625 mmol) was treated with fumaric acid (Aldrich, 73 mg, 0.63 mmol) in EtOAc/MeOH (v.10:1, 10 mL) at ambient temperature for 10 hours to give title compound (240.2 mg, 85%). 1H NMR (300 MHz, MeOH-D4) δ 1.87-2.22 (m, 3H), 2.31-2.45 (m, 1H), 2.60-2.67 (m, 1H), 3.30-3.50 (m, 5H), 3.89-4.00 (m, 1H), 5.49-5.57 (m, 1H), 6.57 (d, J=3.1 Hz, 1H), 6.68 (s, 2H), 7.28-7.35 (m, 2H), 7.52 (d, J=8.5 Hz, 1H), 7.74 (dd, J=8.6, 1.9 Hz, 1H), 8.11-8.19 (m, J=9.5 Hz, 2H) ppm. MS (DCI/NH3) m/z 321 (M+H)+. Anal. Calculated for C19H20N4O.1.0 C4O4H4.0.50 H2O: C, 62.01; H, 5.66; N, 12.58. Found: C, 61.79; H, 5.46; N, 12.43.

Sources & evidence

ORD record
ord-ea2f922c24de40c085870350bb5335d7
Source dataset
uspto-grants-2010_02
Patent number
US07655657B2

Reaction notes

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