Sodium Carbonate → HCID 67406540, compound

HRID 1401264Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[O:13][C:14]2[C:19]([C:20](=[O:22])[CH:21]=1)=[C:18]([O:23]C)[CH:17]=[C:16]([O:25]C)[C:15]=2[C@@H:27]1[CH2:31][CH2:30][N:29]([CH3:32])[C@H:28]1[CH2:33][OH:34].Cl.N1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CO>[Cl:1][C:2]1[C:7]([C:8]([F:9])([F:11])[F:10])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[O:13][C:14]2[C:19]([C:20](=[O:22])[CH:21]=1)=[C:18]([OH:23])[CH:17]=[C:16]([OH:25])[C:15]=2[C@@H:27]1[CH2:31][CH2:30][N:29]([CH3:32])[C@H:28]1[CH2:33][OH:34]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of compound of example 40 (0.560 g, 1.12 mmol) and pyridine hydrochloride (0.700 g, 6.05 mmol) was heated at 180° C. for a period of 2.5 hours. The reaction mixture was diluted with methanol (60 mL) and basified with solid Na2CO3 to pH 10. The reaction mixture was filtered, and washed with methanol. The organic layer was concentrated and the residue purified by column chromatography using 0.01% ammonia and 4.5% methanol in chloroform as eluent to afford the title compound.

Workup

filtrationThe reaction mixture was filtered
washwashed with methanol
concentrationThe organic layer was concentrated
customthe residue purified by column chromatography

Sources & evidence

ORD record: ord-c6c97e05b2484c3b8109c0814fc5c691
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906953B2

Reaction notes

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