Acetic Acid → HCID 86631936, compound

HRID 906053Notes

Reaction equation

HRID 906053 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[CH:13]=[C:12]([C:14]([NH2:16])=[O:15])[CH:11]=[CH:10][C:9]=2[C:17]([NH2:19])=[O:18])[CH2:3][CH2:2]1.[CH:20](=O)[CH3:21].C([BH3-])#N.[Na+].C(O)(=O)C>CO.O>[CH2:20]([N:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[CH:13]=[C:12]([C:14]([NH2:16])=[O:15])[CH:11]=[CH:10][C:9]=2[C:17]([NH2:19])=[O:18])[CH2:3][CH2:2]1)[CH3:21]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86631937HCID 86631937, compound

Product 1

HCID 86631936HCID 86631936, compoundYield 19.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of N4-[8-(5-acetylpyridin-2-yl)-8-azabicyclo[3.2.1]oct-3-endo-yl]-2-(piperidin-4-ylamino)benzene-1,4-dicarboxamide (130 mg, 0.28 mmol) in methanol were added acetaldehyde (12 mg, 0.28 mmol), sodium cyanoborohydride (18 mg, 0.28 mmol) and acetic acid (17 mg, 0.28 mmol) at room temperature. The reaction mixture was stirred at room temperature for 2 h. Then the reaction mixture was poured into water (250 mL), extracted with ethyl acetate (2×50 mL), dried over sodium sulfate, filtered and concentrated to a volume of 10 mL. The precipitate thus formed was collected by filtration to give N4-[8-(5-acetylpyridin-2-yl)-8-azabicyclo[3.2.1]oct-3-endo-yl]-2-[(1-ethylpiperidin-4-yl)amino]benzene-1,4-dicarboxamide (16 mg, 12% yield). 1H NMR (400 MHz, methanol-d4): 8.70 (s, 1H), 8.06 (d, J=9.2 Hz, 1H), 7.69 (d, J=8.2 Hz, 1H), 7.14 (s, 1H), 6.98 (d, J=8.2 Hz, 1H), 6.77 (d, J=9.2 Hz, 1H), 4.70 (br, s, 2H), 4.02 (m, 1H), 3.82-3.45 (m, 2H), 3.20-3.05 (m, 6H), 3.00 (s, 6H), 2.53 (s, 3H), 2.40-2.1 (m, 10H), 2.05 (m, 2H), 1.34 (t, J=7.2 Hz, 3H). MS (EI) for C29H38N6O3: 519 (MH+).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to a volume of 10 mL
  5. customThe precipitate thus formed
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-395a9ab3af124998a3a008a7b6c9c4d6
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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