Acetic Acid → HCID 57874433, compound

HRID 1093841Notes

Reaction equation

HRID 1093841 reaction equation
C=O.Cl.[O:4]=[C:5]([N:21]1[CH2:26][CH2:25][CH:24]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)[CH2:23][CH2:22]1)[CH2:6][NH:7][C:8]([C:10]1[N:11]=[N:12][N:13]([CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH:14]=1)=[O:9].[C:38](O)(=O)C.N>O.[Zn]>[O:4]=[C:5]([N:21]1[CH2:22][CH2:23][CH:24]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:35])([F:36])[F:37])[CH:29]=2)[CH2:25][CH2:26]1)[CH2:6][NH:7][C:8]([C:10]1[N:11]=[N:12][N:13]([CH:15]2[CH2:16][CH2:17][N:18]([CH3:38])[CH2:19][CH2:20]2)[CH:14]=1)=[O:9]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 712FormaldehydeHCID 66591622HCID 66591622, compound

Product 1

HCID 57874433HCID 57874433, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

37% Aqueous formaldehyde (29.22 mg, 0.97 mmol) solution was added to a stirred solution of 1-piperidin-4-yl-1H-[1,2,3]triazole-4-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide hydrochloride (252 mg, 0.48 mmol) in a mixture of acetic acid (240 mg, 4.0 mmol) and H2O (2 mL) and stirring was continued at ambient temperature for 5 minutes. Zinc dust was added to the reaction mixture (94.1 mg, 1.44 mmol) and stirring was continued at ambient temperature for 1 hr. The reaction mixture was cooled, basified with aqueous ammonia solution and extracted with DCM. The organic layer was collected and dried over sodium sulfate and concentrated under reduced pressure to afford 110 mg (45.6% Yield) of 1-(1-methyl-piperidin-4-yl)-1H-[1,2,3]triazole-4-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 495.2. 1H NMR (300 MHz, DMSO-d6): δ 8.7 (s, 1H), 8.3 (t, 1H), 7.5 (t, 1H), 7.3 (t, 3H), 4.8 (m, 1H), 4.5 (m, 1H), 4.2 (d, 2H), 3.9 (m, 1H), 3.7 (m, 1H), 3.4 (m, 2H), 2.9 (m, 2H), 2.2 (s, 3H), 2.1 (m, 6H), 1.95 (m, 2H).

Workup

  1. stirringstirring
  2. waitwas continued at ambient temperature for 1 hr
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with DCM
  5. customThe organic layer was collected
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4166763e2a3847bf80266049083e4597
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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