Isopropenyl chloroformate → Prop-1-en-2-yl (4-(4-(4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamido)-2,5-difluorophenoxy)pyridin-2-yl)carbamate

HRID 1411157Notes

Reaction equation

HRID 1411157 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:14]([F:15])=[CH:13][C:12]([NH:16][C:17]([C:19]3[C:20](=[O:35])[N:21]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH:22]=[CH:23][C:24]=3[O:25][CH2:26][CH3:27])=[O:18])=[C:11]([F:36])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.Cl[C:38]([O:40][C:41]([CH3:43])=[CH2:42])=[O:39]>N1C=CC=CC=1>[CH2:26]([O:25][C:24]1[CH:23]=[CH:22][N:21]([C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)[C:20](=[O:35])[C:19]=1[C:17]([NH:16][C:12]1[C:11]([F:36])=[CH:10][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:38](=[O:39])[O:40][C:41]([CH3:43])=[CH2:42])[CH:7]=2)=[C:14]([F:15])[CH:13]=1)=[O:18])[CH3:27]

Participants

4

Reactant 2

HCID 93846Isopropenyl chloroformateHCID 68252797N-(4-((2-Aminopyridin-4-yl)oxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

Product 1

HCID 86703365Prop-1-en-2-yl (4-(4-(4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamido)-2,5-difluorophenoxy)pyridin-2-yl)carbamateYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-(4-((2-Aminopyridin-4-yl)oxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (0.12 g, 0.24 mmol) was dissolved in pyridine (2 mL), treated with isopropenyl chloroformate (0.030 mL, 0.27 mmol), and stirred at RT overnight. The solution was concentrated to obtain crude prop-1-en-2-yl (4-(4-(4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamido)-2,5-difluorophenoxy)pyridin-2-yl)carbamate which was used for the next reaction (assuming 100% yield).

Workup

  1. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-da4706bc10a84eeba8169d4bf3258557
Source dataset
uspto-grants-2014_12
Patent number
US08921565B2

Reaction notes

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