Cesium carbonate → HCID 66997775, compound

HRID 18014Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH2:10][N:11]([CH2:37][CH2:38][CH2:39][CH2:40]OS(C)(=O)=O)[C:12]([C:14]1[NH:15][C:16](=[O:36])[C:17]([O:34][CH3:35])=[C:18]2[C:23]=1[CH2:22][CH2:21][N:20]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[C:27]([Cl:32])[CH:26]=1)[C:19]2=[O:33])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:32][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][C:28]=1[F:31])[CH2:24][N:20]1[CH2:21][CH2:22][C:23]2[C:18](=[C:17]([O:34][CH3:35])[C:16](=[O:36])[N:15]3[CH2:40][CH2:39][CH2:38][CH2:37][N:11]([CH2:10][CH2:9][O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:12](=[O:13])[C:14]3=2)[C:19]1=[O:33]

Participants

Conditions

Temperature: 75 °C

Procedure

To a mixture of N-[2-(benzyloxy)ethyl]-N-(4-methanesulfonyloxybutyl)-6-(3-chloro-4-fluorobenzyl)-4-methoxy-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide (90 mg, 0.14 mmol) and cesium carbonate (53 mg, 0.16 mmol) in DMF was heated at 75° C. for 90 minutes. The product mixture was concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 5% methanol in dichloromethane. Collection and concentration of appropriate fractions afforded the title compound.

Workup

concentrationThe product mixture was concentrated under vacuum
customCollection and concentration of appropriate fractions

Sources & evidence

ORD record: ord-f706c24310ea48e6a9029e2a496afbd2
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741315B2

Reaction notes

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