Water → HCID 86713630, compound

HRID 1430457Notes

Reaction equation

HRID 1430457 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:15]3[C:16]([CH3:32])=[CH:17][C:18]([F:31])=[C:19]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:23])[CH:20]=3)[C:8](=[O:14])[N:9]2[CH2:12][CH3:13])=[CH:4][N:3]=1.Cl[C:34]([O:36][C:37]([CH3:39])=[CH2:38])=[O:35].O>N1C=CC=CC=1>[CH2:12]([N:9]1[C:10]2[C:5](=[CH:4][N:3]=[C:2]([NH:1][C:34](=[O:35])[O:36][C:37]([CH3:39])=[CH2:38])[CH:11]=2)[CH:6]=[C:7]([C:15]2[CH:20]=[C:19]([NH:21][C:22]([NH:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:23])[C:18]([F:31])=[CH:17][C:16]=2[CH3:32])[C:8]1=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 93846Isopropenyl chloroformateHCID 86713631HCID 86713631, compound

Product 1

HCID 86713630HCID 86713630, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-(5-(7-amino-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluoro-4-methylphenyl)-3-phenylurea (0.35 g, 0.811 mmol) in pyridine (5 mL) was treated with isopropenyl chloroformate (0.147 g, 1.217 mmol) and stirred at RT for 1 h. Water was added, the mixture stirred for 10 minutes and the resulting solid was collected via filtration and dried to afford prop-1-en-2-yl (1-ethyl-3-(4-fluoro-2-methyl-5-(3-phenylureido)phenyl)-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl)carbamate (360 mg, 86% yield). MS (ESI) m/z: 516.2 [M+H]+.

Workup

  1. stirringthe mixture stirred for 10 minutes
  2. filtrationthe resulting solid was collected via filtration
  3. customdried

Sources & evidence

ORD record
ord-c283d08e9f894e5f8357172306dc411e
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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