HCID 68182884, compound → HCID 68183401, compound

HRID 1615557Notes

Reaction equation

C([N:4]1[C@@H:9]([C:10]([O:12][CH3:13])=[O:11])[C@H:8]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[C:7]2[CH:22]=[C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[S:24][C:6]=2[C:5]1=[O:31])C=C>C(O)CC.[Rh](Cl)(Cl)Cl>[Cl:21][C:16]1[CH:15]=[C:14]([C@H:8]2[C@H:9]([C:10]([O:12][CH3:13])=[O:11])[NH:4][C:5](=[O:31])[C:6]3[S:24][C:23]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[CH:22][C:7]2=3)[CH:19]=[CH:18][C:17]=1[Cl:20]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of methyl rel-(4R,5R)-6-allyl-4-(3,4-dichlorophenyl)-2-(morpholin-4-yl)-7-oxo-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-5-carboxylate (0.344 g, 0.714 mmol) and rhodium(III)chloride, (22.2 mg, 0.106 mmol) in 1-propanol (9.0 mL) was heated in a sealed tube under argon at 120° C. for 50 h. The reaction mixture was evaporated and purified by silica gel chromatography to afford the product as a white solid (0.278 g, 88%). LCMS: (AA), ES+: 441, 443, 1H NMR (400 MHz, CDCl3) δ 7.38 (d, J=8.3 Hz, 1H), 7.34-7.25 (m, 1H), 7.04 (dd, J=8.3, 2.0 Hz, 1H), 5.68 (s, 1H), 5.57 (s, 1H), 4.59 (d, J=2.9 Hz, 1H), 4.20-4.19 (m, 1H), 3.81-3.79 (m, 4H), 3.74 (s, 3H), 3.20-3.18 (m, 4H).

Workup

customThe reaction mixture was evaporated
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-a6b06724939948e7afe4aae5b9735942
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765746B2

Reaction notes

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