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 1050873Notes

Reaction equation

HRID 1050873 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-1e2ba095fb8043949af0ff32571d92b9
Source dataset
uspto-grants-2016_07
Patent number
US09387202B2

Reaction notes

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