Pyridine → HCID 86713640, compound

HRID 1430488Notes

Reaction equation

HRID 1430488 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][C:11]1[C:12]([F:42])=[CH:13][C:14]([F:41])=[C:15]([C:17]2[C:18](=[O:40])[N:19]([CH2:38][CH3:39])[C:20]3[C:25]([CH:26]=2)=[CH:24][N:23]=[C:22]([N:27]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[CH3:28])[CH:21]=3)[CH:16]=1.N1C=CC=CC=1.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O.O>[CH3:37][O:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][N:27]([CH3:28])[C:22]2[CH:21]=[C:20]3[C:25]([CH:26]=[C:17]([C:15]4[C:14]([F:41])=[CH:13][C:12]([F:42])=[C:11]([NH:10][C:8]([NH:7][C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)=[O:9])[CH:16]=4)[C:18](=[O:40])[N:19]3[CH2:38][CH3:39])=[CH:24][N:23]=2)=[CH:31][CH:32]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 7672Phenyl isocyanateHCID 516892Sodium BicarbonateHCID 89611458HCID 89611458, compound

Product 1

HCID 86713640HCID 86713640, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phenyl isocyanate (58 mg, 0.488 mmol) was added to a solution of Example A7 (200 mg, 0.444 mmol) and pyridine (140 mg, 1.776 mmol) in THF (5 mL) and the mixture was stirred at RT overnight. The mixture was diluted with EtOAc, water and satd. NaHCO3; the resulting precipitate was collected by filtration, washed with EtOAc and dried in vacuo to give 1-(5-(7-((4-methoxybenzyl)(methyl)amino)-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2,4-difluorophenyl)-3-phenylurea (219 mg, 87% yield). MS (ES-API) m/z: 570.2 [M+H]+.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with EtOAc
  3. customdried in vacuo

Sources & evidence

ORD record
ord-09cb8e79a4ef4899a1f2edca26e5d55e
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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