Bromine → HCID 11462335, compound

HRID 1441427Notes

Reaction equation

HRID 1441427 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]1[N:15]=[N:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)=[CH:12][CH:11]=1)[CH2:2]2.[C:23]([S-:25])#[N:24].[K+].BrBr>CC(O)=O>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]1[N:15]=[N:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]4[N:22]=[C:23]([NH2:24])[S:25][C:18]=4[CH:17]=3)=[CH:12][CH:11]=1)[CH2:2]2

Participants

5

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 114037154-{6-[(3R)-1-Aza-bicyclo[2.2.2]oct-3-yloxy]-pyridazin-3-yl}-phenylamine

Product 1

HCID 11462335HCID 11462335, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The product of Example 24F (150 mg, 0.5 mmol) was treated with KSCN (Aldrich, 97 mg, 1 mmol) and bromine (Aldrich, 96 mg, 0.6 mmol) in HOAc (5 mL) at ambient temperature for 0.5 h. It was then quenched with Na2SO3 (aq. 10%, 1 mL) and concentrated. The title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.1) as solid (170 mg, yield, 80%). 1H NMR (300 MHz, CD3OD) δ 1.60-1.70 (m, 1H), 1.72-1.98 (m, 2H), 2.02-2.19 (m, 1H), 2.23-2.42 (m, 1H), 2.82-3.13 (m, 5H), 3.42-3.68 (m, 1H), 5.15-5.54 (m, 1H), 7.26 (d, J=9.2 Hz, 1H), 7.49 (d, J=8.5 Hz, 1H), 7.87 (dd, J=8.6, 1.9 Hz, 1H), 8.07 (d, J=9.5 Hz, 1H), 8.23 (d, J=1.4 Hz, 1H) ppm. MS (DCI/NH3): 354 (M+H)+.

Workup

  1. customIt was then quenched with Na2SO3 (aq. 10%, 1 mL)
  2. concentrationconcentrated
  3. customThe title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.1) as solid (170 mg, yield, 80%)

Sources & evidence

ORD record
ord-fb53edd2318642d589555ea9d22df580
Source dataset
uspto-grants-2010_02
Patent number
US07655657B2

Reaction notes

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