Lithium perchlorate → phenylmethyl[((3S)-1-{(2R)-2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-2-hydroxyethyl}-3-pyrrolidinyl)methyl]carbamate

HRID 639078Notes

Reaction equation

[F:1][C:2]1[C:11]([C@H:12]2[CH2:14][O:13]2)=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([O:15][CH3:16])=[N:9]2)=[N:4][CH:3]=1.[C:17]1([CH2:23][O:24][C:25](=[O:33])[NH:26][CH2:27][C@@H:28]2[CH2:32][CH2:31][NH:30][CH2:29]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl([O-])(=O)(=O)=O.[Li+]>C(#N)C>[C:17]1([CH2:23][O:24][C:25](=[O:33])[NH:26][CH2:27][C@@H:28]2[CH2:32][CH2:31][N:30]([CH2:14][C@@H:12]([C:11]3[C:10]4[C:5](=[CH:6][CH:7]=[C:8]([O:15][CH3:16])[N:9]=4)[N:4]=[CH:3][C:2]=3[F:1])[OH:13])[CH2:29]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 43 °C

Procedure

To a solution of 7-fluoro-2-(methyloxy)-8-[(2S)-2-oxiranyl]-1,5-naphthyridine (220 mg, 1.0 mmol) in acetonitrile (5 mL) were added phenylmethyl[(3R)-3-pyrrolidinylmethyl]carbamate (235 mg, 1.0 mmol) followed by Lithium perchlorate (106 mg, 1.0 mmol). After heated at 43° C. for 48 h, the resulting mixture was cooled down to room temperature, concentrated and purified with column chromatography (silica, 1-5% methanol in DCM (1% NH4OH)) to provide the title compound as an off-white solid (250 mg, 55%): LC/MS (ES) m/e 455 (M+H)+.

Workup

temperaturethe resulting mixture was cooled down to room temperature
concentrationconcentrated
custompurified with column chromatography (silica, 1-5% methanol in DCM (1% NH4OH))

Sources & evidence

ORD record: ord-cfc7313c19db48eaa3f092efc64edce5
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691850B2

Reaction notes

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