Benzylamine → tert-butyl 9-(2-(2-(benzylcarbamoyl)-3-chloro-1H-pyrrol-1-ylamino)-2-oxoethyl)-9H-purin-6-ylcarbamate

HRID 525047Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=[O:11])[O:8][C:7]([CH2:12][N:13]1[CH:21]=[N:20][C:19]3[C:14]1=[N:15][CH:16]=[N:17][C:18]=3[N:22](C(OC(C)(C)C)=O)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[N:6]2.[CH2:37]([NH2:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>O1CCOCC1>[CH2:37]([NH:44][C:9]([C:10]1[N:5]([NH:6][C:7](=[O:8])[CH2:12][N:13]2[CH:21]=[N:20][C:19]3[C:14]2=[N:15][CH:16]=[N:17][C:18]=3[NH:22][C:23](=[O:24])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:4]=[CH:3][C:2]=1[Cl:1])=[O:11])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution di-tert-butyl 9-((5-chloro-4-oxo-4H-pyrrolo[1,2-d][1,3,4]oxadiazin-2-yl)methyl)-9H-purin-6-ylimidodicarbonate (100 mg, 0.2 mmol) in 2 mL of dry 1,4-dioxane under argon atmosphere 127 μL of benzylamine (1.16 mmol) were added and the mixture was stirred at 30° C. during 2 hours. At the end of this period, the reaction mixture was concentrated to dryness under reduced pressure and the residue was purified by flash chromatography silica (dichloromethane/methanol). After purification were obtained 95 mg of tert-butyl 9-(2-(2-(benzylcarbamoyl)-3-chloro-1H-pyrrol-1-ylamino)-2-oxoethyl)-9H-purin-6-ylcarbamate (92% yield).

Workup

concentrationAt the end of this period, the reaction mixture was concentrated to dryness under reduced pressure
customthe residue was purified by flash chromatography silica (dichloromethane/methanol)
customAfter purification

Sources & evidence

ORD record: ord-a030397dccdb4540ab2c789841f34f30
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340547B2

Reaction notes

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