methyl 6-(methylthio)nicotinate → HCID 58368201, compound

HRID 2365262Notes

Reaction equation

HRID 2365262 reaction equation
O[C@H]1CCCC[C@@H]1N1C[C:15]2[C:14]3C=CC=C[C:13]=3[C:12](CC3C=NC(SC)=CC=3)=[CH:11][C:10]=2[C:9]1=[O:30].BrC1C2C=CC=CC=2C2CN([C@H]3CCCC[C@@H]3O)C(=O)C=2C=1.CS[C:55]1[CH:64]=[CH:63][C:58]([C:59]([O:61][CH3:62])=[O:60])=[CH:57][N:56]=1>>[CH2:9]([O:30][C:55]1[N:56]=[CH:57][C:58]([C:59]([O:61][CH3:62])=[O:60])=[CH:63][CH:64]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 901959methyl 6-(methylthio)nicotinateHCID 68622221HCID 68622221, compoundHCID 68626060HCID 68626060, compound

Product 1

HCID 58368201HCID 58368201, compound

Procedure

The title compound was prepared employing the procedures described for the construction of 2-[(1S,2S)-2-hydroxycyclohexyl]-5-{[6-(methylthio)pyridine-3-yl]methyl}-1,2-dihydro-3H-benzo[e]isoindol-3-one in Example 10, substituting 5-bromo-8-[(1S,2S)-2-hydroxycyclohexyl]-8,9-dihydro-7H-pyrrolo[3,4-h]quinolin-7-one for 5-bromo-2-[(1S,2S)-2-hydroxycyclohexyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one, and substituting methyl 6-(benzyloxy)pyridine-3-carboxylate for methyl 6-(methylthio)nicotinate. The resultant white solid gave a proton NMR spectra consistent with theory: 1H NMR (400 MHz, CDCl3) δ 9.00-8.98 (m, 1H), 8.43-8.41 (m, 1H), 8.06 (s, 1H), 7.80 (s, 1H), 7.54-7.51 (m, 1H), 7.45-7.42 (m, 2H), 7.38-7.28 (m, 4H), 6.70 (d, J=8.5 Hz, 1H), 5.33 (s, 2H), 5.30-4.87 (m, 2H), 4.38 (s, 2H), 4.23-4.17 (m, 1H), 3.79-3.73 (m, 1H), 2.22-2.19 (m, 1H), 2.01-1.98 (m, 1H), 1.86-1.83 (m, 2H), 1.73-1.63 (m, 1H), 1.54-1.31 (m, 3H) ppm.

Workup

  1. customThe resultant white solid gave a proton NMR spectra consistent with theory

Sources & evidence

ORD record
ord-fa0f5973262a4090a3884ec8ac2885a1
Source dataset
uspto-grants-2014_04
Patent number
US08697690B2

Reaction notes

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