Ammonia → HCID 11267180, compound

HRID 1372864Notes

Reaction equation

HRID 1372864 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.[NH:17]1[C:25]2[C:20](=[CH:21][C:22](B(O)O)=[CH:23][CH:24]=2)[CH:19]=[CH:18]1.N>>[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:21]=[C:20]4[C:25](=[CH:24][CH:23]=3)[NH:17][CH:18]=[CH:19]4)=[CH:7][N:6]=1)[CH2:10]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 27343615-Indolylboronic acidHCID 67069973(3S)-3-[(5-Bromopyrimidin-2-yl)oxy]-1-azabicyclo[2.2.2]octane

Product 1

HCID 11267180HCID 11267180, compound

Procedure

The product of Example 13E (283 mg, 1 mmol) was coupled with 5-indolylboronic acid (193 mg, 1.2 mmol) according to the procedure of Example 3A, The title product was purified by preparative HPLC (Gilson, column, Symmetry® C-8 7 μm, 40×100 mm. Eluting Solvent, MeCN/H2O (with 0.2% v. TFA) (v. 90/10 to 10/90 over 20 min.) Flow rate, 75 mL/min., uv, 250 nm) as solid (120 mg, yield, 38%). 1H NMR (300 MHz, CD3OD) δ 1.50–1.63 (m, 1H), 1.66–1.92 (m, 2H), 2.03–2.18 (m, 1H), 2.24–2.32 (m, 1H), 2.75–3.07 (m, 5H), 3.38–3.49 (m, 1H), 5.13–5.21 (m, 1H), 6.53 (dd, J=3.0, 0.7 Hz, 1H), 7.30 (d, J=3.4 Hz, 1H), 7.35 (dd, J=8.5, 1.7 Hz, 1H), 7.51 (dt, J=9.2, 0.7 Hz, 1H), 7.80 (dd, J=1.7, 0.7 Hz, 1H), 8.81 (s, 2H) ppm. MS (DCl/NH3): m/z 321 (M+H)+.

Workup

  1. customThe title product was purified by preparative HPLC (Gilson, column, Symmetry® C-8 7 μm, 40×100 mm
  2. customEluting Solvent, MeCN/H2O (with 0.2% v. TFA) (v. 90/10 to 10/90 over 20 min.) Flow rate, 75 mL/min., uv, 250 nm) as solid (120 mg, yield, 38%)

Sources & evidence

ORD record
ord-e86027f1ab83424d9caa7ac4e99b3385
Source dataset
uspto-grants-2007_01
Patent number
US07160876B2

Reaction notes

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