5-Chloro-2-iodopyridine → 3-Amino-1-(5-chloropyridin-2-yl)-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one

HRID 593481Notes

Reaction equation

HRID 593481 reaction equation
[O:1]=[C:2]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[C:7]2[CH:15]=[CH:16][CH:17]=[CH:18][C:6]=2[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:4][CH:3]1[NH:25]C(=O)OCC1C=CC=CC=1.[Cl:36]C1C=CC(I)=NC=1>>[NH2:25][CH:3]1[C:2](=[O:1])[N:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:36])=[CH:11][N:10]=2)[C:7]2[CH:15]=[CH:16][CH:17]=[CH:18][C:6]=2[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:4]1

Participants

3

Reactant 2

HCID 111181485-Chloro-2-iodopyridineHCID 90082795benzyl 2-oxo-5-phenyl-1-(pyridin-2-yl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylcarbamate

Product 1

HCID 900802943-Amino-1-(5-chloropyridin-2-yl)-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one

Procedure

Intermediate 2A was prepared as described in Intermediate 1A using 5-chloro-2-iodopyridine. The racemate was purified by preparative SFC chromatography (Berger SFC MGII, CHIRALCEL® OJ-H 250×30 mm ID, 5 μm, 80/20 CO2/MeOH, 85 mL/min) to give Intermediate 3A. RT=3.44 min (H2O/CH3OH with TFA, CHROMOLITH® ODS S5 4.6×50 mm, gradient=3 min, wavelength=220 and 254 nm); MS(ES):m/z=497 [M+H+].

Workup

  1. customThe racemate was purified by preparative SFC chromatography (Berger SFC MGII, CHIRALCEL® OJ-H 250×30 mm ID, 5 μm, 80/20 CO2/MeOH, 85 mL/min)

Sources & evidence

ORD record
ord-e4aa5ba10b9a4521924b4e125ed1cef8
Source dataset
uspto-grants-2016_01
Patent number
US09242940B2

Reaction notes

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