HCID 178516879, compound → HCID 178516893, compound

HRID 539549Notes

Reaction equation

HRID 539549 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][CH2:19][C:20]3[N:21]=[N:22][NH:23][CH:24]=3)=[C:9]([O:25]CC3C=CC=CC=3)[C:8]2=[O:33])[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][CH2:19][C:20]3[N:21]=[N:22][NH:23][CH:24]=3)=[C:9]([OH:25])[C:8]2=[O:33])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 178516879HCID 178516879, compoundHCID 178516889HCID 178516889, compound

Product 1

HCID 178516893HCID 178516893, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of 158f (0.22 g, 0.50 mmol) in anhydrous THF as described for synthesis of 159b gave 159f (0.13 g, 74%) of pure product. 1H NMR (400 MHz, DMSO) δ 8.91 (s, 1H), 8.57 (s, 1H), 7.82 (d, J=7.4 Hz, 2H), 7.42 (t, J=7.6 Hz, 2H), 7.31 (t, J=7.3 Hz, 1H), 7.09 (d, J=6.6 Hz, 1H), 6.64 (d, J=7.0 Hz, 1H), 6.04 (t, J=6.9 Hz, 1H), 4.36 (t, J=7.0 Hz, 2H), 3.86 (t, J=7.2 Hz, 2H), 1.83 (m, 2H), 1.61 (m, 2H), 1.26 (m, 6H). 13C NMR (100 MHz, CDCl3) δ 158.80, 147.89, 147.00, 130.88, 129.05, 128.30, 127.12, 125.87, 119.83, 114.13, 107.10, 50.48, 50.05, 30.37, 29.20, 28.67, 26.46, 26.42. HRMS (FAB) calcd for C20H25N4O2 [M+H]+ 353.1977. found 353.1992.

Sources & evidence

ORD record
ord-4d60536d8b4543029113ffd346b84f7a
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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