Isopropyl chloroformate → Isopropyl 4-(2,6-dichlorobenzamido)pyridin-2-ylcarbamate

HRID 449876Notes

Reaction equation

HRID 449876 reaction equation
Cl[C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3].[NH2:8][C:9]1[CH:14]=[C:13]([NH:15][C:16](=[O:25])[C:17]2[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:24])[CH:12]=[CH:11][N:10]=1>N1C=CC=CC=1>[Cl:24][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([Cl:23])[C:17]=1[C:16]([NH:15][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([NH:8][C:2](=[O:3])[O:4][CH:5]([CH3:7])[CH3:6])[CH:14]=1)=[O:25]

Participants

4

Reactant 2

HCID 7917Isopropyl chloroformateHCID 59618313N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide

Product 1

HCID 59618162Isopropyl 4-(2,6-dichlorobenzamido)pyridin-2-ylcarbamateYield 19%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of isopropyl chloroformate (0.066 g, 0.53 mmol) in 3 ml of pyridine was added N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide (0.1 g, 0.36 mmol). The resulting mixture was stirred for another 30 min and then concentrated under reduced pressure. 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: 19%). 1H NMR (DMSO-d6, 500 MHz): δ 11.17 (s, 1H), 9.97 (s, 1H), 8.21-8.17 (m, 2H), 7.61-7.53 (m, 3H), 7.40 (m, 1H), 4.90 (m, 1H), 1.25 (t, J=5.5 Hz, 6H). LCMS (ESI) m/z: 368.0 [M+H+].

Workup

  1. concentrationconcentrated under reduced pressure
  2. 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-77c5531a5525407cb974d323834a6661
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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