HCID 178516876, compound → HCID 178516890, compound

HRID 539546Notes

Reaction equation

HRID 539546 reaction equation
[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]3[N:18]=[N:19][NH:20][CH:21]=3)=[C:9]([O:22]CC3C=CC=CC=3)[C:8]2=[O:30])[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][C:17]3[N:18]=[N:19][NH:20][CH:21]=3)=[C:9]([OH:22])[C:8]2=[O:30])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 178516876HCID 178516876, compoundHCID 178516889HCID 178516889, compound

Product 1

HCID 178516890HCID 178516890, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of 158c (0.25 g, 0.62 mmol) in anhydrous THF as described for synthesis of 159b gave 159c (0.12 g, 63%) of pure product. 1H NMR (400 MHz, CDCl3) δ 7.79 (m, 3H), 7.41 (t, J=7.6 Hz, 2H), 7.32 (t, J=7.4 Hz, 1H), 6.76 (m, 3H), 6.13 (t, J=7.2 Hz, 1H), 4.45 (t, J=6.8 Hz, 2H), 4.02 (t, J=7.1 Hz, 2H), 1.99 (m, 2H), 1.82 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 158.47, 147.63, 146.62, 130.41, 128.69, 127.99, 126.60, 125.53, 119.80, 114.15, 107.10, 49.38, 48.57, 27.02, 26.01. HRMS (EI) calcd for C17H18N4O2 [M]+ 310.1430. found 310.1425.

Sources & evidence

ORD record
ord-2d79f2ef56224e74b6ce0a8818a71bbf
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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