2-Amino-5-chloropyridine → HCID 67040866, compound

HRID 605067Notes

Reaction equation

HRID 605067 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:37])[NH:17][C:18]3[CH:23]=[CH:22][C:21]([S:24][C:25]4[CH:30]=[CH:29][C:28]([C:31](Cl)=[O:32])=[CH:27][C:26]=4[N+:34]([O-:36])=[O:35])=[CH:20][CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl:38][C:39]1[CH:40]=[CH:41][C:42]([NH2:45])=[N:43][CH:44]=1.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:37])[NH:17][C:18]3[CH:23]=[CH:22][C:21]([S:24][C:25]4[CH:30]=[CH:29][C:28]([C:31](=[O:32])[NH:45][C:42]5[CH:41]=[CH:40][C:39]([Cl:38])=[CH:44][N:43]=5)=[CH:27][C:26]=4[N+:34]([O-:36])=[O:35])=[CH:20][CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 661742-Amino-5-chloropyridineHCID 81531DiisopropylethylamineHCID 86615543HCID 86615543, compound

Product 1

HCID 67040866HCID 67040866, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of Example 19C (471 mg, 0.861 mmol) in anhydrous tetrahydrofuran (8 mL) was treated with 5-chloro-2-aminopyridine (125 mg, 0.972 mmol) and diisopropylethylamine (0.232 mL, 1.332 mmol), and stirred at room temperature under a nitrogen atmosphere for 18 hours. The solvent was removed by rotary evaporation in vacuo, the residue taken up in ethyl acetate (250 mL) and washed with saturated aqueous sodium bicarbonate (50 mL), water (2×50 mL), and brine (50 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Trituration with methylene chloride provided the title compound as a yellow solid (373 mg, 61%).

Workup

  1. customThe solvent was removed by rotary evaporation in vacuo
  2. washwashed with saturated aqueous sodium bicarbonate (50 mL), water (2×50 mL), and brine (50 mL)
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5148834cdcd49bb9e32700995e32edf
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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