Fumaric Acid → HCID 87137705, compound

HRID 1817015Notes

Reaction equation

HRID 1817015 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][C:17]#[N:18])[C:12]([Br:15])=[N:13][CH:14]=3)[CH2:8][C@H:2]12.[C:19]([OH:26])(=[O:25])/[CH:20]=[CH:21]/[C:22]([OH:24])=[O:23]>CO.C(OCC)C>[C:19]([OH:26])(=[O:25])/[CH:20]=[CH:21]/[C:22]([OH:24])=[O:23].[NH:1]1[CH2:5][CH2:4][C@@H:3]2[CH2:6][N:7]([C:9]3[CH:10]=[C:11]([CH2:16][C:17]#[N:18])[C:12]([Br:15])=[N:13][CH:14]=3)[CH2:8][C@H:2]12

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 9922595HCID 9922595, compound

Product 1

HCID 87137705HCID 87137705, compoundYield 15.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

The product of Example 66C (70.0 mg, 0.228 mmol) in 10% CH3OH in diethyl ether (5 mL) was treated with fumaric acid (26.4 mg, 0.228 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 (15 mg, 0.0347 mmol, 15% yield). 1H NMR (CH3OH-d4, 300 MHz) δ 2.04 (m, 1H), 2.34 (m, 1H), 3.33 (m, 3H), 3.45 (m, 3H), 3.83 (dd, J=11.9, 1.7 Hz, 1H), 3.95 (s, 2H), 4.38 (m, 1H), 6.68 (s, 2H), 7.27 (d, J=3.1 Hz, 1H), 7.82 (d, J=3.1 Hz, 1H); MS (DCI/NH3) m/z 307 (M+H−C4H4O4)+; Anal. calculated for C13F15BrN4.C4H4O4.0.5H2O: C, 47.24; H, 4.66; N, 12.96. Found: C, 47.39; H, 4.37; N, 12.76.

Workup

  1. customthe precipitate was isolated via filtration

Sources & evidence

ORD record
ord-d8862b641b2b4ac6a1c0f2564dd18399
Source dataset
uspto-grants-2009_10
Patent number
US07598236B2

Reaction notes

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