Acetic Acid → HCID 117600859, compound

HRID 1497731Notes

Reaction equation

HRID 1497731 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:17][NH2:18].C1COCC1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1(C)C=CC(S(O)(=O)=O)=CC=1.ClCCl>[Cl:8][C:5]1[N:6]=[CH:7][C:2]([NH2:1])=[C:3]([CH:9]([NH:18][CH3:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:4]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 6329MethylamineHCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 59654927HCID 59654927, compound

Product 1

HCID 117600859HCID 117600859, compound

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidSolventHCID 6344DichloromethaneSolvent

Procedure

(5-Amino-2-chloro-pyridin-4-yl)-phenyl-methanone (360 mg, 1.547 mmol), methylamine in THF (4.5 mL, 2 M, 9.00 mmol), p-toluene sulfonic acid in acetic acid (225 mg, 12%, 0.157 mmol) are stirred at room temperature in dichloromethane (15 mL). Sodium triacetoxyborohydride (1.92 g, 9.06 mmol) is added in three separate portions over 24 hours. The reaction mixture is quenched with saturated sodium carbonate solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate. The drying agent is removed by filtration. The solvent is removed in vacuo and the residue is purified by column chromatography on silica gel using a dichloromethane and methanol gradient. This provides the desired compound as a yellow solid.

Workup

  1. customseparate portions over 24 hours
  2. customThe reaction mixture is quenched with saturated sodium carbonate solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customThe drying agent is removed by filtration
  6. customThe solvent is removed in vacuo
  7. customthe residue is purified by column chromatography on silica gel using a dichloromethane and methanol gradient

Sources & evidence

ORD record
ord-c2675d0ecc704e099cd4d4d053c39641
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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