Ethyl chloroformate → HCID 90077618, compound

HRID 2203256Notes

Reaction equation

HRID 2203256 reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([CH2:7][NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14]3[C:19]([C:20]=2[NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)=[N:18][C:17]([Cl:32])=[CH:16][CH:15]=3)=[O:10])=[CH:5][CH:4]=1.Cl[C:36](OCC)=[O:37]>>[Cl:32][C:17]1[CH:16]=[CH:15][C:14]2[N:13]=[CH:12][C:11]3[C:9](=[O:10])[N:8]([CH2:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:34][CH:33]=4)[C:36](=[O:37])[N:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:30])[F:31])[CH:23]=4)[C:20]=3[C:19]=2[N:18]=1

Participants

3

Reactant 2

HCID 10928Ethyl chloroformateHCID 90077617HCID 90077617, compound

Product 1

HCID 90077618HCID 90077618, compound

Procedure

N-(4-methoxybenzyl)-6-chloro-4-(3-(trifluoromethyl)phenylamino)-1,5-naphthyridine-3-carboxamide (4.5 g, 9.2 mmol) is suspended in ethyl chloroformate (50 mL). The resulting mixture was added to 90° C., stirred for 120 hrs, rotary-evaporated to remove the volatile substance, and separated by silicagel column chromatography (EtOAc/PE=0-1/4) to obtain a yellow oil of 9-chloro-3-(4-methoxybenzyl)-1-(3-(trifluoromethyl)phenyl)pyrimido[5,4-c][1,5]naphthyridine-2,4(1H,3H)-dione (700 mg).

Workup

  1. additionThe resulting mixture was added to 90° C.
  2. customrotary-evaporated
  3. customto remove the volatile substance
  4. customseparated by silicagel column chromatography (EtOAc/PE=0-1/4)

Sources & evidence

ORD record
ord-c92b8732057d4ad78f11e431905e68ab
Source dataset
uspto-grants-2016_06
Patent number
US09365572B2

Reaction notes

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