Isopropanol → HCID 74767736, compound

HRID 533920Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N:12]2[CH2:16][CH2:15][C@@H:14]([O:17][C:18]3[CH:19]=[N:20][C:21]([OH:24])=[CH:22][CH:23]=3)[C:13]2=[O:25])[CH:5]=[C:6]2[C:10]=1[CH2:9][CH2:8][C:7]2=[O:11].[CH:26](O)([CH3:28])[CH3:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.C(Cl)Cl.CN1C(=O)CCC1>[F:1][C:2]1[CH:3]=[C:4]([N:12]2[CH2:16][CH2:15][C@@H:14]([O:17][C:18]3[CH:19]=[N:20][C:21]([O:24][CH:26]([CH3:28])[CH3:27])=[CH:22][CH:23]=3)[C:13]2=[O:25])[CH:5]=[C:6]2[C:10]=1[CH2:9][CH2:8][C:7]2=[O:11]

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of (R)-1-(7-fluoro-3-oxo-indan-5-yl)-3-(6-hydroxy-pyridin-3-yloxy)-pyrrolidin-2-one (60 mg), isopropanol (30 mg) and solvent (THF/DCM/NMP 4:4:1, 5 mL) under argon was added triphenyiphosphine (polymer, 0.4 mmol). After 5 minutes DIAD (51 mg) was added. The mixture was shaken at 40° C. for 12 hours. The mixture was filtered and the filtrate was concentrated. The residue was purified by preparative HPLC to provide Example 2-24. 1H-NMR (400 MHz, DMSO) δ 7.99 (1H, dd, J=11.1, 1.8 Hz), 7.97 (1H, d, J=3.1 Hz), 7.77 (1H, d, J=1.8 Hz), 7.51 (1H, dd, J=9.0, 3.1 Hz), 6.71 (1H, d, J=9.0 Hz), 5.22 (1H, dd, J=8.3, 8.3 Hz), 5.14 (1H, m), 3.96 (1H, m), 3.85 (1H, m), 3.10 (2H, m), 2.72 (2H, m), 2.69 (1H, m), 2.14 (1H, m), 1.27 (6H, d, J=6.2 Hz).

Workup

filtrationThe mixture was filtered
concentrationthe filtrate was concentrated
customThe residue was purified by preparative HPLC
customto provide Example 2-24

Sources & evidence

ORD record: ord-aabe532c296b41dfba94c7059bc1e9b5
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853412B2

Reaction notes

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