Pyridinium hydrobromide → HCID 71576560, compound

HRID 1484471Notes

Reaction equation

HRID 1484471 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([F:16])=[CH:13][CH:14]=2)[C:9](=[O:17])[NH:8][C:7]=1[C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1.[BrH:29].[NH+]1C=CC=CC=1>C1COCC1>[NH2:2][CH2:3][CH2:4][O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([F:16])=[CH:13][CH:14]=2)[C:9](=[O:17])[NH:8][C:7]=1[C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:25][CH2:26][CH2:27][CH2:28]2)=[C:20]([Br:29])[CH:19]=1

Participants

4

Reactant 2

HCID 21226041Pyridinium hydrobromideHCID 89587862HCID 89587862, compound2×

Product 1

HCID 71576560HCID 71576560, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 4-(2-aminoethoxy)-7-fluoro-3-(4-pyrrolidin-1-yl-phenyl)-2H-isoquinolin-1-one hydrochloride [(I), cpd. 7, R=R1=R2=H, R3=4-pyrrolidin-1-yl, R4=H](15 mg, 0.037 mmol) in dry THF (0.3 mL), kept at room temperature, pyridinium hydrobromide perbromide (13 mg, 0.04 mmol) were added. The reaction mixture was stirred for 1 hour, the volatiles were then evaporated in vacuo and the resulting crude was purified through preparative HPLC on a Phenomenex Gemini C18 (21×250 mm, 10 μm) column, using a Waters FractionLynx System equipped with a 2996 PDA detector and ZQ2000 single quadrupole mass spectrometer, with electrospray ionization (positive and negative mode). Mobile phase A was 0.05% NH3/ACN 95/5, and mobile phase B was ACN. Gradient from 5 to 95% B in 25 min, hold 95% B 3 min. Flow rate 20 mL/min.

Workup

  1. customkept at room temperature
  2. customthe volatiles were then evaporated in vacuo
  3. customthe resulting crude was purified through preparative HPLC on a Phenomenex Gemini C18 (21×250 mm, 10 μm) column
  4. customequipped with a 2996 PDA detector and ZQ2000 single quadrupole mass spectrometer, with electrospray ionization (positive and negative mode)
  5. waitGradient from 5 to 95% B in 25 min
  6. custom95% B 3 min

Sources & evidence

ORD record
ord-f9e90302756e42e284a13e83da0b908e
Source dataset
uspto-grants-2016_08
Patent number
US09422243B2

Reaction notes

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