Diisopropylethylamine → HCID 90410749, compound

HRID 1848757Notes

Reaction equation

F[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][N:8]=1.Cl.[Br:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[C:24]([F:30])[CH:23]=1.CCN(C(C)C)C(C)C>C(#N)C>[Br:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH:27][C:2]2[CH:3]=[C:4]([O:5][CH2:6][C:7]3[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][N:8]=3)[CH:14]=[CH:15][C:16]=2[N+:17]([O-:19])=[O:18])=[C:24]([F:30])[CH:23]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 2-((3-fluoro-4-nitrophenoxy)methyl)-5-methylpyridine (1.50 g, 5.72 mmol), 4-bromo-2-fluorobenzylamine hydrochloride (1.51 g, 6.29 mmol), DIPEA (2.96 mL, 17.2 mmol) and acetonitrile (19.1 mL) was sealed in reaction vessel and heated to 75° Celsius for 18 h. The mixture was then cooled to RT, transferred to a round bottomed flask and concentrated to dryness. The resulting residue was then heated in a minimum amount of i-PrOH to 70° Celsius until homogeneous. The resulting solution was then cooled to RT where yellow solids precipitated, which were collected by filtration. (2.40 g, 94%). MS (ESI): mass calcd. for C20H17BrFN3O3, 445.04; m/z found, 446.0 [M+H]+.

Workup

customwas sealed in reaction vessel
temperatureThe mixture was then cooled to RT
customtransferred to a round bottomed flask
concentrationconcentrated to dryness
temperatureThe resulting residue was then heated in a minimum amount of i-PrOH to 70° Celsius until homogeneous
temperatureThe resulting solution was then cooled to RT where yellow solids
customprecipitated
filtrationwhich were collected by filtration

Sources & evidence

ORD record: ord-cb433c9f6ab94a39ad7bc6b0ed327a65
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952177B2

Reaction notes

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