Bromide ion → HCID 10363337, compound

HRID 720439Notes

Reaction equation

HRID 720439 reaction equation
O[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]2[C:11]([C:22]([F:25])([F:24])[F:23])=[N:12][N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:7]=2[C:6]1=[O:26].P(Br)(Br)Br.[Br-].[CH3:32][NH:33][CH3:34]>C(Cl)Cl>[CH3:32][N:33]([CH3:34])[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]2[C:11]([C:22]([F:23])([F:25])[F:24])=[N:12][N:13]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[C:7]=2[C:6]1=[O:26]

Participants

6

Reactant 4

HCID 259Bromide ionHCID 674DimethylamineHCID 24614Phosphorus tribromideHCID 21891459HCID 21891459, compound

Product 1

HCID 10363337HCID 10363337, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Part B: 6-(3-Hydroxy-propyl)-1-(4-methoxy-phenyl)-3-trifluoromethyl-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one (0.200 g, 0.542 mmol) and phosphorus tribromide (0.077 mL, 0.812 mmol) were dissolved in methylene chloride (20 mL) and stirred at rt for 2 hr. The reaction was quenched with water (100 mL), extracted with methylene chloride (3×100 mL), washed with saturated NaHCO3 (1×100 mL), washed with brine (1×100 mL), dried over Na2So4, and concentrated to afford 0.096 g (41%). The bromide intermediate (0.048 g, 0.111 mmol) was redissolved in methylene chloride (6 mL), and 2M dimethylamine (0.389 mL, 0.777) was added. The reaction was stirred at rt overnight. The reaction was evaporated, redissolved in toluene (15 mL), and re-concentrated. Purification was performed by reverse phase HPLC and freeze-dried to afford the title compound (0.014 g, 32%): 1H NMR (CDCl3) δ 7.43 (d, j=8.8 Hz, 2H), 6.96 (d, j=9.1 Hz, 2H), 3.85 (s, 3H), 3.71 (t, j=7.0 Hz, 2H), 3.56 (t, j=6.6 Hz, 2H), 3.08–2.98 (m, 4H), 2.80(s, 6H), 2.15–2.02 (m, 2H) ppm; Mass Spec 397.4(M+H)+.

Workup

  1. customThe reaction was quenched with water (100 mL)
  2. extractionextracted with methylene chloride (3×100 mL)
  3. washwashed with saturated NaHCO3 (1×100 mL)
  4. washwashed with brine (1×100 mL)
  5. customdried over Na2So4
  6. concentrationconcentrated
  7. customto afford 0.096 g (41%)
  8. stirringThe reaction was stirred at rt overnight
  9. customThe reaction was evaporated
  10. dissolutionredissolved in toluene (15 mL)
  11. concentrationre-concentrated
  12. customPurification
  13. customfreeze-dried

Sources & evidence

ORD record
ord-2936595a9b4c4f4681142bd314028e33
Source dataset
uspto-grants-2006_11
Patent number
US07135469B2

Reaction notes

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