HCID 178516877, compound → HCID 178516891, compound

HRID 539547Notes

Reaction equation

HRID 539547 reaction equation
[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]3[N:19]=[N:20][NH:21][CH:22]=3)=[C:9]([O:23]CC3C=CC=CC=3)[C:8]2=[O:31])[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][C:18]3[N:19]=[N:20][NH:21][CH:22]=3)=[C:9]([OH:23])[C:8]2=[O:31])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 178516877HCID 178516877, compoundHCID 178516889HCID 178516889, compound

Product 1

HCID 178516891HCID 178516891, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of 158d (0.085 g, 0.20 mmol) in anhydrous THF as described for synthesis of 159b gave 159d (0.045 g, 68%) of pure product. 1H NMR (400 MHz, DMSO) δ 8.56 (s, 1H), 7.82 (d, J=8.1 Hz, 2H), 7.43 (t, J=7.7 Hz, 2H), 7.32 (t, J=7.4 Hz, 1H), 7.10 (dd, J=6.8, 1.6 Hz, 1H), 6.65 (dd, J=7.2, 1.5 Hz, 1H), 6.05 (1, J=7.0 Hz, 1H), 4.38 (t, J=7.0 Hz, 2H), 3.89 (t, J=7.2 Hz, 2H), 1.89 (m, 2H), 1.67 (m, 2H), 1.25 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 158.44, 147.67, 146.61, 130.51, 128.72, 128.01, 126.71, 125.57, 119.54, 113.81, 106.86, 49.86, 49.38, 29.58, 28.31, 23.19. HRMS (FAB) calcd for C18H21N4O2 [M+H]+ 325.1664. found 325.1683.

Sources & evidence

ORD record
ord-4ec4f776ed5b42cdb389601401566ad1
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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