Potassium Carbonate → HCID 86713671, compound

HRID 1430532Notes

Reaction equation

[NH2:1][C:2]1[C:3]([F:28])=[CH:4][C:5]([F:27])=[C:6]([C:8]2[C:9](=[O:26])[N:10]([CH2:24][CH3:25])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][C:19](=[O:23])[CH2:20][C:21]#[N:22])[CH:12]=3)[CH:7]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:36]([O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:37]>C1COCC1>[C:21]([CH2:20][C:19]([NH:18][C:13]1[CH:12]=[C:11]2[C:16]([CH:17]=[C:8]([C:6]3[C:5]([F:27])=[CH:4][C:3]([F:28])=[C:2]([NH:1][C:36](=[O:37])[O:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[CH:7]=3)[C:9](=[O:26])[N:10]2[CH2:24][CH3:25])=[CH:15][N:14]=1)=[O:23])#[N:22]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of N-(3-(5-amino-2,4-difluorophenyl)-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl)-2-cyanoacetamide (0.5 g, 1.3 mmol) and K2CO3 (448 mg, 3.25 mmol) in THF (4 mL) was treated drop-wise with phenyl chloroformate (408 mg, 2.6 mmol) and heated at 60° C. overnight. The mixture was cooled to RT, concentrated to dryness, treated with water and extracted with EtOAc (2×). The combined organics were washed with brine, dried over Na2SO4, concentrated and purified via silica gel chromatography to afford phenyl (5-(7-(2-cyanoacetamido)-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2,4-difluorophenyl)carbamate (400 mg, 61% yield).

Workup

temperatureThe mixture was cooled to RT
concentrationconcentrated to dryness
additiontreated with water
extractionextracted with EtOAc (2×)
washThe combined organics were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
custompurified via silica gel chromatography

Sources & evidence

ORD record: ord-b7e5c93acfb748ec8766906480ec171f
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940756B2

Reaction notes

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