3-Aminophenylboronic acid → HCID 11277880, compound

HRID 970002Notes

Reaction equation

HRID 970002 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([O:8][C@H:9]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]2)=[N:6][CH:7]=1.[NH2:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1>>[N:11]12[CH2:16][CH2:15][CH:14]([CH2:13][CH2:12]1)[C@H:9]([O:8][C:5]1[N:4]=[CH:3][C:2]([C:22]3[CH:23]=[C:18]([CH:19]=[CH:20][CH:21]=3)[NH2:17])=[CH:7][N:6]=1)[CH2:10]2

Participants

3

Reactant 2

HCID 922693-Aminophenylboronic acidHCID 67069973(3S)-3-[(5-Bromopyrimidin-2-yl)oxy]-1-azabicyclo[2.2.2]octane

Product 1

HCID 11277880HCID 11277880, compound

Procedure

The product of Example 22A (284 mg, 1.0 mmol) was treated with 3-aminophenylboronic acid (Lancaster, 276 mg, 2.0 mmol) according to the procedure of Example 1B. The title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.1) as solid (285 mg, yield, 96%). 1H NMR (300 MHz, MeOH-d4) δ 1.48-1.62 (m, 1H), 1.61-1.91 (m, 2H), 2.01-2.16 (m, 1H), 2.22-2.30 (m, 1H), 2.74-3.05 (m, 5H), 3.36-3.47 (m, 1H), 5.12-5.20 (m, 1H), 6.75 (ddd, J=8.2, 2.1, 1.0 Hz, 1H), 6.89 (ddd, J=7.4, 1.7, 1.0 Hz, 1H), 6.93 (t, J=1.8 Hz, 1H), 7.20 (t, J=7.8 Hz, 1H), 8.74 (s, 2H) ppm. MS (DCl/NH3) m/z 297 (M+H)+.

Workup

  1. customThe title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.1) as solid (285 mg, yield, 96%)

Sources & evidence

ORD record
ord-af1137c16d0b47b6aa02610885a21d7e
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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