Pyridine → HCID 86706036, compound

HRID 2280262Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:23]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)=[CH:22][N:21]([CH2:30][CH2:31][OH:32])[N:20]=2)=[CH:15][CH:14]=1.N1C=CC=CC=1.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>C(Cl)Cl>[CH3:39][S:40]([O:32][CH2:31][CH2:30][N:21]1[CH:22]=[C:23]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[C:19]([C:16]2[CH:15]=[CH:14][C:13]([O:12][CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][N:6]=4)[N:1]=3)=[CH:18][CH:17]=2)=[N:20]1)(=[O:42])=[O:41]

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of Intermediate 5B, 2-(3-(4-((1,5-naphthyridin-2-yl)methoxy)phenyl)-4-(pyridin-4-yl)-1H-pyrazol-1-yl)ethanol in DCM is cooled at 0° C. Pyridine (12 equivalents) and methanesulfonyl chloride (8 equivalents) are added and the reaction mixture is stirred at 0° C. for 1 h. The mixture is quenched with water and extracted with more DCM. The organic solvent is separated, dried (MgSO4), and concentrated under reduced pressure. The crude residue is purified by silica gel column chromatography. The desired fractions are collected and concentrated under reduced pressure to yield 2-(3-(4-((1,5-naphthyridin-2-yl)methoxy)phenyl)-4-(pyridin-4-yl)-1H-pyrazol-1-yl)ethyl methanesulfonate.

Workup

customThe mixture is quenched with water
extractionextracted with more DCM
customThe organic solvent is separated
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure
customThe crude residue is purified by silica gel column chromatography
customThe desired fractions are collected
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-237f084fea8e492db74e6a3add84a8c7
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09138494B2

Reaction notes

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