Triphenylphosphine → HCID 74767654, compound

HRID 533917Notes

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)[CH2:13]2)[CH:5]=[C:6]2[C:10]=1[CH2:9][CH2:8][C:7]2=[O:11].[O:25]1[CH2:30][CH2:29][CH:28](O)[CH2:27][CH2:26]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC([O:54]C(/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:28]4[CH2:29][CH2:30][O:25][CH2:26][CH2:27]4)=[CH:22][CH:23]=3)[C:13]2=[O:54])[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-(60 mg), tetrahydro-pyran-4-ol (51 mg) and solvent (THF/DCM/NMP 4:4:1, 5 mL) under argon was added triphenylphosphine (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 2-07. 1H-NMR (400 MHz, DMSO) δ 7.99 (1H, dd, J=11.2, 1.8 Hz), 7.97 (1H, d, J=3.1 Hz), 7.78 (1H, d, J=1.8 Hz), 7.54 (1H, dd, J=9.0, 3.1 Hz), 6.78 (1H, d, J=9.0 Hz), 5.23 (1H, dd, J=8.3, 8.3 Hz), 5.08 (1H, m), 3.96 (1H, m), 3.86 (1H, m), 3.86 (2H, m), 3.10 (2H, m), 2.73 (2H, m), 2.70 (1H, m), 2.13 (1H, m), 1.98 (2H, m), 1.60 (2H, m).

Workup

filtrationThe mixture was filtered
concentrationthe filtrate was concentrated
customThe residue was purified by preparative HPLC
customto provide Example 2-07

Sources & evidence

ORD record: ord-e971797f43994c069ef43559a6eb68b1
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853412B2

Reaction notes

Loading…