2-Amino-4-methylpyridine → HCID 178428579, compound

HRID 1059892Notes

Reaction equation

HRID 1059892 reaction equation
[CH:1]([C:3]1[S:7][C:6]([NH:8][C:9]([NH2:11])=[NH:10])=[N:5][C:4]=1[CH3:12])=O.[NH2:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:35]CCl>CN(C)C=O>[ClH:35].[ClH:35].[CH3:20][C:18]1[CH:17]=[CH:16][N:15]=[C:14]([NH:13][CH2:1][C:3]2[S:7][C:6]([NH:8][C:9]([NH2:11])=[NH:10])=[N:5][C:4]=2[CH3:12])[CH:19]=1

Participants

6

Reactant 4

HCID 15332-Amino-4-methylpyridineHCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 178433189HCID 178433189, compound

Product 1

HCID 178428579HCID 178428579, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-formyl-2-guanidino-4-methylthiazole (1.0 g) and 2-amino-4-picoline (587 mg) in N,N-dimethylformamide (10 ml) and dichloromethane (60 ml) was added sodium triacetoxyborohydride (1.82 g), and the mixture was stirred for 140 hours. The mixture was evaporated under reduced pressure, and to the residue was added hydrochloric acid (1N, 12 ml). The pH was adjusted to 12 with 4N aqueous sodium hydroxide. The mixture was extracted with ethyl acetate twice. The combined organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 50 g, 5% methanol in dichloromethane), and the fractions containing objective compound were combined and evaporated. The residue was dissolved in ethanol, and to the solution was added a solution of hydrogen chloride in 1,4-dioxane (4N, 2 ml). The precipitate was collected by filtration, washed with ethyl acetate-ethanol (1:1, 3 ml) and dried to give N-(5-(4-methylpyridin-2-ylaminomethyl)-4-methylthiazol-2-yl)-guanidine dihydrochloride (513 mg).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. additionto the residue was added hydrochloric acid (1N, 12 ml)
  3. extractionThe mixture was extracted with ethyl acetate twice
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel 50 g, 5% methanol in dichloromethane)
  8. additionthe fractions containing objective compound
  9. customevaporated
  10. dissolutionThe residue was dissolved in ethanol
  11. additionto the solution was added a solution of hydrogen chloride in 1,4-dioxane (4N, 2 ml)
  12. filtrationThe precipitate was collected by filtration
  13. washwashed with ethyl acetate-ethanol (1:1, 3 ml)
  14. customdried

Sources & evidence

ORD record
ord-c1a17002af644e95a1379831c579b985
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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