Water → HCID 67955376, compound

HRID 872294Notes

Reaction equation

[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([O:18][C:19]4[C:24]([CH:25]=[O:26])=[CH:23][CH:22]=[CH:21][N:20]=4)=[C:13]([C:14]([F:17])([F:16])[F:15])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1.[CH3:27][Mg]Br.O>O1CCCC1>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([O:18][C:19]4[C:24]([CH:25]([OH:26])[CH3:27])=[CH:23][CH:22]=[CH:21][N:20]=4)=[C:13]([C:14]([F:16])([F:15])[F:17])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

2-{[1-(Cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazol-5-yl]oxy}pyridine-3-carbaldehyde (417, 20 mg, 0.055 mmol, 1 equiv.) was dissolved in tetrahydrofuran (2 mL), cooled to 0° C. and treated with methylmagnesium bromide (28 μL, 0.083 mmol, 1.5 equiv). After stirring for 30 minutes, the mixture was poured into water (10 mL) and was extracted with ethyl acetate (3×20 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified via preparative reverse phase HPLC (gradient 80:20 to 5:95; water containing 0.05% trifluoroacetic acid:acetonitrile containing 0.05% trifluoroacetic acid) to provide the titled compound 418. High resolution mass spectrometry (ES+) m/z=379.1374, [(M+H)+ calculated for C18H18F3N4O2: 379.1376].

Workup

extractionwas extracted with ethyl acetate (3×20 mL)
dry with materialThe combined organic extracts were dried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified via preparative reverse phase HPLC (gradient 80:20 to 5:95; water containing 0.05% trifluoroacetic acid:acetonitrile containing 0.05% trifluoroacetic acid)

Sources & evidence

ORD record: ord-975607bbd45d4ebbb78d7d2c44e4368a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975286B2

Reaction notes

Loading…