Water → HCID 22037815, compound

HRID 1790019Notes

Reaction equation

HRID 1790019 reaction equation
[CH:1]1([N:6]2[C:10]3=[CH:11][N:12]=[N:13][C:14]([NH2:15])=[C:9]3[CH:8]=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:16]Br.[OH-].[Na+].O>ClCCl>[Br:16][C:8]1[C:9]2[C:10](=[CH:11][N:12]=[N:13][C:14]=2[NH2:15])[N:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24408Bromine2×HCID 22037820HCID 22037820, compound

Product 1

HCID 22037815HCID 22037815, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 1-cyclopentyl-1H-pyrrolo[2,3-d]pyridazin-4-amine (0.595 mg, approx. 60% pure, 1.76 mmol) in dichloromethane (100 mL) was treated with a solution of dichloromethane (5 mL) containing bromine (0.5 g, 2.95 mmol) over the course of 1.25 hours. The mixture was stirred an additional one hour then another portion of dichloromethane (3 mL) containing bromine (0.3 g) was added. The mixture was stirred for 2.5 hours then treated with 5 mL 5N aqueous sodium hydroxide and 25 mL water. The layers were separated and the organic layer was concentrated under reduced pressure to give a residue which was purified by reverse phase preparative HPLC to give 3-bromo-1-cyclopentyl-1H-pyrrolo[2,3-d]pyridazin-4-amine (168 mg, 35%); 1H NMR (DMSO-d6, 400 MHz) δ 8.94 (s, 1H), 7.79 (s, 1H), 6.11 (bs, 2H), 4.94 (m, 1H), 2.12 (m, 2H), 1.83 (m, 4H), 1.67 (m, 2H); 5%–100% acetonitrile-0.05 M ammonium acetate over 25 min, 1 mL/min) tr 11.25 min.; LC/MS: MH+ 282.8.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for 2.5 hours
  3. customThe layers were separated
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customto give a residue which
  6. customwas purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-a4b076179dca456485413d3e1e416279
Source dataset
uspto-grants-2006_07
Patent number
US07071199B1

Reaction notes

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