Fumaric Acid → HCID 86584382, compound

HRID 1817013Notes

Reaction equation

HRID 1817013 reaction equation
[NH:1]1[CH2:5][CH2:4][C@@H:3]2[CH2:6][N:7]([C:9]3[CH:10]=[C:11]([CH2:16][OH:17])[C:12]([Br:15])=[N:13][CH:14]=3)[CH2:8][C@H:2]12.[C:18]([OH:25])(=[O:24])/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22]>CO.C(OCC)C>[C:18]([OH:25])(=[O:24])/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22].[NH:1]1[CH2:5][CH2:4][C@@H:3]2[CH2:6][N:7]([C:9]3[CH:10]=[C:11]([CH2:16][OH:17])[C:12]([Br:15])=[N:13][CH:14]=3)[CH2:8][C@H:2]12

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 9835877HCID 9835877, compound

Product 1

HCID 86584382HCID 86584382, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

The product of Example 64C (90.0 mg, 0.302 mmol) in 20% CH3OH in diethyl ether (10 mL) was treated with a solution of fumaric acid (35.0 mg, 0.302 mmol) in 10% CH3OH in diethyl ether (5 mL). The mixture was stirred for 20 hours and the precipitate was isolated via filtration to provide the title compound (91.3 mg, 0.211 mmol, 70% yield). 1H NMR (CH3OH-d4, 300 MHz) δ 2.05 (in 1H), 2.35 (m, 1H), 3.32 (m, 5H), 3.45 (m, 2H), 3.84 (dd, J=11.5, 1.2 Hz, 1H), 4.39 (m, 1H), 4.57 (s, 2H), 6.67 (s, 2H), 7.33 (d, J=3.1 Hz, 1H), 7.72 (d, J=3.1 Hz, 1H); MS (DCI/NH3) m/z 299 (M+H−C4H4O4)+; Anal. calculated for C12H16BrN3O.C4H4O4.H2O: C, 44.46; H, 5.13; N, 9.72. Found: C, 44.39; H, 4.79; N, 9.66.

Workup

  1. customthe precipitate was isolated via filtration

Sources & evidence

ORD record
ord-fb2ffbb424d94ea8870ee05856c5d419
Source dataset
uspto-grants-2009_10
Patent number
US07598236B2

Reaction notes

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