O-Methylhydroxylamine hydrochloride → (5-fluoropyridin-2-yl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone O-methyl oxime

HRID 473172Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[N:19]=[C:18]([NH:20][C:21]3[CH:25]=[C:24]([CH3:26])[NH:23][N:22]=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)=O)=[N:6][CH:7]=1.Cl.[O:28]([NH2:30])[CH3:29]>CCO>[CH3:29][O:28][N:30]=[C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=1)[C:10]1[N:19]=[C:18]([NH:20][C:21]2[CH:25]=[C:24]([CH3:26])[NH:23][N:22]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a 0.3 M solution of (5-fluoropyridin-2-yl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone from Example 1 in EtOH is added methoxylamine hydrochloride (2 equiv) and the mixture is heated to 60° C. for 30 min or until the reaction is substantially complete. The mixture is concentrated under reduced pressure and the residue is purified by chromatography to afford (5-fluoropyridin-2-yl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone O-methyl oxime. LC-MS (ESI) m/z 377 (M+H)+.

Workup

concentrationThe mixture is concentrated under reduced pressure
customthe residue is purified by chromatography

Sources & evidence

ORD record: ord-0283ce640bde43e188c0a65f9cbf0cca
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633207B2

Reaction notes

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