Formamidine acetate → HCID 86702332, compound

HRID 2279076Notes

Reaction equation

HRID 2279076 reaction equation
[C:1](O)(=O)C.C(N)=N.[F:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:15]([NH:17][C:18]2[N:23]=[C:22]([NH:24][C:25]3[C:26]([O:31][CH3:32])=[N:27][CH:28]=[CH:29][CH:30]=3)[C:21]([NH2:33])=[CH:20][CH:19]=2)[CH3:16])=[N:13][CH:14]=1>C(O)C.C(OCC)(=O)C>[F:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:15]([NH:17][C:18]2[N:23]=[C:22]3[N:24]([C:25]4[C:26]([O:31][CH3:32])=[N:27][CH:28]=[CH:29][CH:30]=4)[CH:1]=[N:33][C:21]3=[CH:20][CH:19]=2)[CH3:16])=[N:13][CH:14]=1

Participants

5

Reactant 2

HCID 160693Formamidine acetateHCID 86702331HCID 86702331, compound

Product 1

HCID 86702332HCID 86702332, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

Formamidine acetate (141 mg, 1.35 mmol) was added to a solution of N6-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]N2-(2-methoxypyridin-3-yl)pyridine-2,3,6-triamine in ethanol (Preparation 22c) and the resulting mixture was heated at 85° C. for 5 hours. The reaction was cooled down and diluted with ethyl acetate (50 mL), washed with brine (2×100 mL) and water (50 mL), dried over magnesium sulphate and the solvent removed under reduced pressure. The residue was purified by flash chromatography (9:1 hexanes/ethyl acetate to 100% ethyl acetate) to give the title compound (104 mg, 84%, two steps) as a green oil.

Workup

  1. temperatureThe reaction was cooled down
  2. washwashed with brine (2×100 mL) and water (50 mL)
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent removed under reduced pressure
  5. customThe residue was purified by flash chromatography (9:1 hexanes/ethyl acetate to 100% ethyl acetate)

Sources & evidence

ORD record
ord-53ff78f329b240bdbe95528bfcaa37b3
Source dataset
uspto-grants-2015_09
Patent number
US09133200B2

Reaction notes

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