1,1'-Carbonyldiimidazole → (3S,11aR)-N-(2,4-difluorobenzyl)-6-methoxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-d]pyrido[1,2-a]pyrazine-8-carboxamide

HRID 338621Notes

Reaction equation

[CH3:1][C@@H:2]1[N:6]2[C:7](=[O:21])[C:8]3[N:9]([CH:11]=[C:12]([C:18]([OH:20])=O)[C:13](=[O:17])[C:14]=3[O:15][CH3:16])[CH2:10][C@H:5]2[O:4][CH2:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[F:34][C:35]1[CH:42]=[C:41]([F:43])[CH:40]=[CH:39][C:36]=1[CH2:37][NH2:38]>COCCOC>[F:34][C:35]1[CH:42]=[C:41]([F:43])[CH:40]=[CH:39][C:36]=1[CH2:37][NH:38][C:18]([C:12]1[C:13](=[O:17])[C:14]([O:15][CH3:16])=[C:8]2[C:7](=[O:21])[N:6]3[C@@H:2]([CH3:1])[CH2:3][O:4][C@@H:5]3[CH2:10][N:9]2[CH:11]=1)=[O:20]

Participants

Conditions

Temperature: 80 °C

Procedure

(3S,11aR)-3-Methyl-6-(methyloxy)-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxylic acid (3.00 g) and 1,1′-carbonyldiimidazole (CDI) (2.15 g) were slurried in 1,2-dimethoxyethane (DME) (30 mL). The mixture was heated to 80° C. for 1 h. The resulting solution was cooled to 20° C., then treated with 2,4-difluorobenzylamine (1.45 mL). After stirring for 1 h, the mixture was quenched with water (30 mL) and DME was removed under reduced pressure. The product was collected by filtration and dried in a vacuum oven overnight at 50° C. The product was obtained as a solid.

Workup

temperatureThe resulting solution was cooled to 20° C.
customthe mixture was quenched with water (30 mL) and DME
customwas removed under reduced pressure
filtrationThe product was collected by filtration
customdried in a vacuum oven overnight at 50° C
customThe product was obtained as a solid

Sources & evidence

ORD record: ord-dc87adf377b640dd99ca943434c07c11
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889877B2

Reaction notes

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