Fumaric Acid → HCID 86584385, compound

HRID 2251451Notes

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-7278866ec7274aef8b6b01ef91982e7c
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319106B2

Reaction notes

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