Fumaric Acid → HCID 66758398, compound

HRID 2251464Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]2[C@H:16]3[C@H:11]([CH2:12][CH2:13][NH:14][CH2:15]3)[CH2:10]2)[CH:6]=[N:7][CH:8]=1.[C:17]([OH:24])(=[O:23])/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21]>>[C:17]([OH:24])(=[O:23])/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]2[C@H:16]3[C@H:11]([CH2:12][CH2:13][NH:14][CH2:15]3)[CH2:10]2)[CH:6]=[N:7][CH:8]=1

Participants

Reactant 2

HCID 444972Fumaric Acid

HCID 9855936HCID 9855936, compound

Product 1

HCID 66758398HCID 66758398, compoundYield 49%

Procedure

The product of Example 88B (1.55 g, 0.710 mmol) and fumaric acid (83 mg, 0.710 mmol) were processed according to the procedure described in Example 66D to provide the title compound (116 mg, 0.346 mmol, 49% yield). 1H NMR (CH3OH-d4, 300 MHz) δ 2.31 (m, 1H), 2.85 (m, 1H), 3.15 (ddd, J=12.6, 8.2, 4.5 Hz, 1H), 3.34 (m, 2H), 3.56 (m, 1H), 3.64 (dd, J=14.2, 1.7 Hz, 1H), 3.79 (dd, J=7.8, 2.7 Hz, 1H), 3.85 (s, 3H), 3.86 (m, 1H), 4.36 (dt, J=8.1, 2.7 Hz, 1H), 6.62 (dd, J=2.2, 2.2 Hz, 1H), 6.68 (s, 2H), 7.55 (d, J=2.2 Hz, 1H), 7.72 (d, J=2.2 Hz, 1H); MS (DCI/NH3) m/z 220 (M+H—C4H4O4)+; Anal. calculated for C12H17N3O.C4H4O4.0.5H2O: C, 55.81; H, 6.44; N, 12.20. Found: C, 55.69; H, 6.10; N, 11.95.

Sources & evidence

ORD record: ord-0974f2fdade745bf937eada1499ff986
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319106B2

Reaction notes

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