Acetic Acid → HCID 57874423, compound

HRID 1093837Notes

Reaction equation

HRID 1093837 reaction equation
C=O.[O:3]=[C:4]([N:19]1[CH2:24][CH2:23][CH:22]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=2)[CH2:21][CH2:20]1)[CH2:5][NH:6][C:7]([C:9]1[N:10]=[N:11][N:12]([CH:14]2[CH2:18][CH2:17][NH:16][CH2:15]2)[CH:13]=1)=[O:8].[C:36](O)(=O)C.N>O.[Zn]>[O:3]=[C:4]([N:19]1[CH2:24][CH2:23][CH:22]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:33])([F:34])[F:35])[CH:27]=2)[CH2:21][CH2:20]1)[CH2:5][NH:6][C:7]([C:9]1[N:10]=[N:11][N:12]([CH:14]2[CH2:18][CH2:17][N:16]([CH3:36])[CH2:15]2)[CH:13]=1)=[O:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 712FormaldehydeHCID 57874467HCID 57874467, compound

Product 1

HCID 57874423HCID 57874423, compoundYield 122.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

37% Aqueous formaldehyde (12 mg, 0.4 mmol) solution was added to a stirred solution of 1-pyrrolidin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide (100 mg, 0.15 mmol) in a mixture of acetic acid (37.62 mg, 0.62 mmol) and H2O (0.5 mL) and stirring was continued at ambient temperature for 5 minutes. To the above mixture was added, Zinc powder (39.23 mg, 0.6 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 thus collected was dried over sodium sulfate and concentrated under reduced pressure to afford 88 mg (88% Yield) of 1-(1-methyl-pyrrolidin-3-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]+: 481.2. 1H NMR (300 MHz, DMSO-d6): δ 11.2-11.0 (b, 1H), 8.85 (s, 1H), 8.4 (s, 1H), 7.5 (t, 1H), 7.3 (t, 3H), 5.51 (b, 1H), 4.7 (m, 2H), 4.4 (d, 2H), 3.8 (m, 1H), 3.7 (m, 2H), 3.4 (m, 2H), 2.9 (s, 3H), 2.5 (m, 2H), 2.0 (m, 2H), 1.7-1.5 (m, 2H).

Workup

  1. additionTo the above mixture was added
  2. waitwas continued at ambient temperature for 1 hr
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with DCM
  5. customThe organic layer thus collected
  6. dry with materialwas dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d7dd97e5e2b64b2088ac92484304804f
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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