Potassium Carbonate → HCID 9800180, compound

HRID 985093Notes

Reaction equation

C([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:19])=[C:16]([CH2:17][OH:18])[N:11]3[CH:10]=[CH:9][C:8]=2[C@@H:7]([O:20][CH2:21][CH2:22][O:23][CH3:24])[C@H:6]([O:25]C(=O)C(C)(C)C)[C@H:5]1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>NC(O)C>[OH:18][CH2:17][C:16]1[N:11]2[CH:10]=[CH:9][C:8]3[C@@H:7]([O:20][CH2:21][CH2:22][O:23][CH3:24])[C@H:6]([OH:25])[C@@H:5]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[NH:4][C:13]=3[C:12]2=[N:14][C:15]=1[CH3:19]

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of 0.60 g (1.10 mmol) of (7R,8R,9R)-10-acetyl-3-hydroxymethyl-7-(2-methoxyethoxy)-2-methyl-9-phenyl-8-pivaloyloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine and 0.30 g (2.10 mmol) potassium carbonate in aminoethanol is stirred at 90° C. for 2 h. The reaction is quenched by adding of saturated aqueous ammonium chloride solution. Subsequently the mixture is extracted twice with dichloromethane. The combined organic layers are washed with brine, dried over sodium sulphate and evaporated in vacuo. The crude product is purified by column chromatography (dichloromethane/methanol: 13/1) to give 0.20 g (0.52 mmol/47%) of the title compound as a colourless solid with a melting point of 180-183° C. (diethyl ether).

Workup

customThe reaction is quenched
additionby adding of saturated aqueous ammonium chloride solution
extractionSubsequently the mixture is extracted twice with dichloromethane
washThe combined organic layers are washed with brine
dry with materialdried over sodium sulphate
customevaporated in vacuo
customThe crude product is purified by column chromatography (dichloromethane/methanol: 13/1)

Sources & evidence

ORD record: ord-846ff704abf941cf818c361e8d6d99b9
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06869949B2

Reaction notes

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