HCID 178516878, compound → HCID 178516892, compound

HRID 539548Notes

Reaction equation

HRID 539548 reaction equation
[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]3[N:20]=[N:21][NH:22][CH:23]=3)=[C:9]([O:24]CC3C=CC=CC=3)[C:8]2=[O:32])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(N2C=CC(CCCC3N=NNC=3)=C(O)C2=O)C=CC=CC=1>C1COCC1>[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]3[N:20]=[N:21][NH:22][CH:23]=3)=[C:9]([OH:24])[C:8]2=[O:32])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 178516878HCID 178516878, compoundHCID 178516889HCID 178516889, compound

Product 1

HCID 178516892HCID 178516892, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of 158e (0.15 g, 0.35 mmol) in anhydrous THF as described for synthesis of 159b gave 159e (0.081 g, 69%) of pure product. 1H NMR (400 MHz, CDCl3) δ 7.81 (m, 3H), 7.42 (m, 2H), 7.32 (m, 1H), 6.77 (m, 2H), 6.12 (t, J=7.1 Hz, 1H), 4.38 (t, J=7.1 Hz, 2H), 3.95 (m, 2H), 1.95 (m, 2H), 1.76 (d, J=7.0 Hz, 2H), 1.39 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 158.20, 147.25, 146.40, 130.30, 128.60, 127.85, 126.65, 125.40, 119.65, 113.90, 106.80, 50.20, 49.60, 30.05, 28.95, 26.00, 25.90. HRMS (FAB) calcd for C19H23N4O2 [M+H]+ 339.1821. found 339.1814.

Sources & evidence

ORD record
ord-d28c8daab43049e0903384c16be444f6
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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