Fumaric Acid → HCID 86584385, compound

HRID 1817016Notes

Reaction equation

[Br:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:15][C@@H:14]3[C@@H:10]([NH:11][CH2:12][CH2:13]3)[CH2:9]2)=[CH:4][C:3]=1[CH2:16][O:17][CH3:18].[C:19]([OH:26])(=[O:25])/[CH:20]=[CH:21]/[C:22]([OH:24])=[O:23]>>[C:19]([OH:26])(=[O:25])/[CH:20]=[CH:21]/[C:22]([OH:24])=[O:23].[Br:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:15][C@@H:14]3[C@@H:10]([NH:11][CH2:12][CH2:13]3)[CH2:9]2)=[CH:4][C:3]=1[CH2:16][O:17][CH3:18]

Participants

Reactant 2

HCID 444972Fumaric Acid

HCID 10267658HCID 10267658, compound

Product 1

HCID 86584385HCID 86584385, compoundYield 78%

Procedure

The product of Example 67B (0.145 g, 0.464 mmol) and fumaric acid (54 mg, 0.464 mmol) were processed according to the procedure described in Example 66D to provide the title compound (0.155 g, 0.362 mmol, 78% yield). 1H NMR (CH3OH-d4, 300 MHz) δ 2.05 (m, 1H), 2.35 (m, 1H), 3.26 (m, 1H), 3.35 (m, 3H), 3.43 (m, 2H), 3.50 (s, 3H), 3.84 (dd, J=11.5, 1.3 Hz, 1H), 4.39 (m, 1H), 4.44 (s, 2H), 6.68 (s, 2H), 7.26 (d, J=3.1 Hz, 1H), 7.74 (d, J=3.1 Hz, 1H); MS (DCI/NH3) m/z 313 (M+H−C4H4O4)+; Anal. calculated for C13H18BrN3O.C4H4O4: C, 47.68; H, 5.18; N, 9.81. Found: C, 47.31; H, 4.93; N, 9.56.

Sources & evidence

ORD record: ord-69fec4afd2c2410ca385c030a53eae45
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598236B2

Reaction notes

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