Fumaric Acid → HCID 21072619, compound

HRID 1441399Notes

Reaction equation

HRID 1441399 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[CH:24]=[C:23]4[C:19]([CH:20]=[CH:21][NH:22]4)=[CH: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[CH2:8][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[CH:24]=[C:23]4[C:19]([CH:20]=[CH:21][NH:22]4)=[CH:18][CH:17]=3)=[CH:12][CH:11]=1)[CH2:2]2

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 11336128HCID 11336128, compound

Product 1

HCID 21072619HCID 21072619, compound

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

The product of Example 5A (30 mg, 0.1 mmol) was treated with fumaric acid (12 mg, 0.1 mmol) in EtOAc/EtOH (v. 1:1, 2 mL) at ambient temperature for 15 h. The title compound was obtained as solid (38.4 mg, yield, 79%). 1H NMR (300 MHz, CD3OD) δ 1.80-2.19 (m, 3H), 2.27-2.40 (m, 1H), 2.48-2.56 (m, 1H), 3.17-3.63 (m, 5H), 3.72-3.83 (m, 1H), 4.80-4.88 (m, 1H), 6.43 (dd, J=3.1, 0.7 Hz, 1H), 6.68 (s, 2H), 7.04 (dt, J=8.8, 2.5 Hz, 2H), 7.21-7.27 (m, 2H), 7.53-7.65 (m, 4H) ppm. MS (DCI/NH3): m/z 319 (M+H)+. Anal. Calcd. for C19H20N4.1.3 C4H4O4: C, 67.05; H, 5.84; N, 5.97. Found: C, 67.15; H, 5.99; N, 5.95.

Sources & evidence

ORD record
ord-37203262e0c9458c8f0c1f7a9a419a1b
Source dataset
uspto-grants-2010_02
Patent number
US07655657B2

Reaction notes

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