Fumaric Acid → HCID 86584388, compound

HRID 1642202Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[C@@H:15]3[C@@H:10]([CH2:11][CH2:12][NH:13][CH2:14]3)[CH2:9]2)=[CH:4][C:3]=1[CH3:16].[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].[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[C@@H:15]3[C@@H:10]([CH2:11][CH2:12][NH:13][CH2:14]3)[CH2:9]2)=[CH:4][C:3]=1[CH3:16]

Participants

Reactant 2

HCID 444972Fumaric Acid

HCID 9942787HCID 9942787, compound

Product 1

HCID 86584388HCID 86584388, compoundYield 33.2%

Procedure

The product of Example 90E (0.130 g, 0.548 mmol) and fumaric acid (64 mg, 0.548 mmol) were processed according to the procedure described in Example 66D to provide the title compound (77 mg, 0.182 mmol, 33% yield). 1H NMR(CH3OH-d4, 300 MHz) δ 2.08 (m, 1H), 2.30 (m, 1H), 2.33 (s, 3H), 2.85 (m, 1H), 3.15 (ddd, J=12.6, 8.2, 4.4 Hz, 1H), 3.30 (m, 1H), 3.57 (ddd, J=12.8, 8.4, 4.0 Hz, 1H), 3.64 (dd, J=14.2, 1.7 Hz, 1H), 3.76 (dd, J=7.1, 2.3 Hz, 1H), 3.84 (t, J=7.4 Hz, 1H), 4.34 (dt, J=8.1, 2.4 Hz, 1H), 6.70 (s, 2H), 7.05 (d, J=2.7 Hz, 1H), 7.57 (d, J=2.7 Hz, 1H); MS (DCI/NH3) m/z 238 (M+H−C4H4O4)+; Anal. calculated for C12H16ClN3.1.6C4H4O4: C, 52.19; H, 5.33; N, 9.92. Found: C, 52.09; H, 5.22; N, 10.10.

Sources & evidence

ORD record: ord-3c3fc74440684eaf8a08133cb6467532
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119635B2

Reaction notes

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