2-(3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-6-chloro-8-methyl-4H-benzo[d][1,3]oxazin-4-one → HCID 11599839, compound

HRID 1348512Notes

Reaction equation

[Br:1][C:2]1[CH:6]=[C:5]([C:7]2[O:12][C:11](=[O:13])[C:10]3[CH:14]=[C:15]([Cl:19])[CH:16]=[C:17]([CH3:18])[C:9]=3[N:8]=2)[N:4]([C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][N:21]=2)[N:3]=1.O1C2C=CC=CC=2CC(=O)N1.[CH3:38][Si:39]([CH2:42][S:43][CH2:44][CH:45]([NH2:47])[CH3:46])([CH3:41])[CH3:40]>O1CCCC1>[Br:1][C:2]1[CH:6]=[C:5]([C:7]([NH:8][C:9]2[C:10]([C:11]([NH:47][CH:45]([CH3:46])[CH2:44][S:43][CH2:42][Si:39]([CH3:41])([CH3:40])[CH3:38])=[O:13])=[CH:14][C:15]([Cl:19])=[CH:16][C:17]=2[CH3:18])=[O:12])[N:4]([C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][N:21]=2)[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-[3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-6-chloro-8-methyl-4H-3,1-benzoxazin-4-one (i.e. the benzoxazinone product of Step E) (0.23 g, 0.51 mmol) in tetrahydrofuran was added 1-trimethylsilylmethylthio-2-propylamine (0.103 g, 0.58 mmol), and the reaction mixture was heated to 80° C. for 3 hours and then cooled to room temperature. The tetrahydrofuran solvent was evaporated under reduced pressure, and the residual solid was chromatographed on silica gel with hexanes/ethyl acetate as eluent (5:1) to afford the title compound, a compound of the present invention, as a white solid (73 mg), m.p. 151–153° C.

Workup

temperaturecooled to room temperature
customThe tetrahydrofuran solvent was evaporated under reduced pressure
customthe residual solid was chromatographed on silica gel with hexanes/ethyl acetate as eluent (5:1)

Sources & evidence

ORD record: ord-2451783c3088478a86caaac2e1b561ff
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211270B2

Reaction notes

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