Fumaric Acid → HCID 66758398, compound

HRID 1817029Notes

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-a11c654951d941df92868247d3fc5f75
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598236B2

Reaction notes

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