Isopropyl isocyanate → 2,6-dichloro-N-(2-(3-isopropylureido)pyridin-4-yl)benzamide

HRID 449877Notes

Reaction equation

[N:1]([CH:4]([CH3:6])[CH3:5])=[C:2]=[O:3].[NH2:7][C:8]1[CH:13]=[C:12]([NH:14][C:15](=[O:24])[C:16]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])[CH:11]=[CH:10][N:9]=1.C(N(C(C)C)CC)(C)C>ClCCCl>[Cl:22][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:23])[C:16]=1[C:15]([NH:14][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([NH:7][C:2]([NH:1][CH:4]([CH3:6])[CH3:5])=[O:3])[CH:13]=1)=[O:24]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-isocyanatopropane (0.050 g, 0.59 mmol), N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide (0.047 g, 0.17 mmol) and diisopropylethylamine (50 mg, 0.39 mmol) in 1,2-dichloroethane (3.0 mL) was stirred at 60° C. for 3 hours. The mixture was concentrated under reduced pressure, and the residue was purified via prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to give the desired product as a white solid (0.025 g, yield: 41%). 1H NMR (DMSO-d6, 500 MHz): δ 8.02 (d, J=5.5 Hz, 1H). 7.51 (s, 1H), 7.40-7.34 (m, 3H), 7.05 (m, 1H), 3.87 (m, 1H), 1.14 (t, J=6.5 Hz, 6H). LCMS (ESI) m/z: 367.1 [M+H+].

Workup

concentrationThe mixture was concentrated under reduced pressure
customthe residue was purified via prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min)

Sources & evidence

ORD record: ord-f74a011483a54392bc0e6ed599f89c20
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486950B2

Reaction notes

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