Fumaric Acid → HCID 66758398, compound

HRID 1642200Notes

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-77547cabc342432194a3397c2c4d1f4a
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119635B2

Reaction notes

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