2-Iodopyridine → HCID 90087878, compound

HRID 593483Notes

Reaction equation

[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:4][CH:3]1[NH:22]C(=O)OCC1C=CC=CC=1.I[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1>>[NH2:22][C@@H:3]1[C:2](=[O:1])[N:8]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:4]1

Participants

Reactant 2

HCID 2211262-Iodopyridine

HCID 118345344HCID 118345344, compound

Product 1

HCID 90087878HCID 90087878, compound

Procedure

Intermediate 3E was prepared from Intermediate 3D and 2-iodopyridine according to the procedure described for Example 1. The racemate was purified by preparative SFC chromatography (Berger SFC MGII, OD-H 250×30 mm ID, 5 μm, 73/17 CO2/MeOH, 85 mL/min) to give Intermediate 4E. RT=1.668 min (H2O/CH3OH with TFA, CHROMOLITH® ODS S5 4.6×50 mm, gradient=3 min, wavelength=220 and 254 nm); MS(ES):m/z=373.2 [M+H+].

Workup

customThe racemate was purified by preparative SFC chromatography (Berger SFC MGII, OD-H 250×30 mm ID, 5 μm, 73/17 CO2/MeOH, 85 mL/min)

Sources & evidence

ORD record: ord-000cdc06fe774c0eac05206c2e0a4885
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242940B2

Reaction notes

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