3-Fluoroaniline → HCID 57874374, compound

HRID 1093783Notes

Reaction equation

HRID 1093783 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH:12]=[C:13]([N:17]2[CH:21]=[C:20]([C:22]([OH:24])=O)[N:19]=[N:18]2)[CH:14]=[CH:15][CH:16]=1.FC1C=C(C=CC=1)N.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:55][CH2:56][C:57]([N:59]1[CH2:64][CH2:63][CH:62]([O:65][C:66]2[CH:71]=[CH:70][CH:69]=[C:68]([C:72]([F:75])([F:74])[F:73])[CH:67]=2)[CH2:61][CH2:60]1)=[O:58]>CN(C=O)C.O>[O:58]=[C:57]([N:59]1[CH2:60][CH2:61][CH:62]([O:65][C:66]2[CH:71]=[CH:70][CH:69]=[C:68]([C:72]([F:75])([F:73])[F:74])[CH:67]=2)[CH2:63][CH2:64]1)[CH2:56][NH:55][C:22]([C:20]1[N:19]=[N:18][N:17]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([F:10])[CH:12]=2)[CH:21]=1)=[O:24]

Participants

9

Reactant 6

HCID 97423-FluoroanilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 28743195HCID 28743195, compoundHCID 665915472-Amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochloride

Product 1

HCID 57874374HCID 57874374, compoundYield 77.46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (168 mg, 1.3 mmol) was added to a stirred solution of 1-(3-fluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid (prepared by the method used for the synthesis of Intermediate 64, starting from 3-fluoroaniline) (60 mg, 0.29 mmol) in DMF (5 mL) followed by, HOBt (43 mg, 0.32 mmol) and EDCI (139 mg, 0.72 mmol). After 2 minutes of stirring, 2-amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochloride salt (prepared according to Step 1 and 5 of the General Scheme) (108 mg, 0.32 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the precipitate formed was collected to afford 110 mg (77.46% Yield) of 1-(3-fluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 492.16, 90.71%. 1H NMR (300 MHz, DMSO-d6): δ 9.4 (s, 1H), 8.56 (t, 1H), 8.0 (q, 2H), 7.74 (q, 1H), 7.58 (t, 1H), 7.46-7.24 (m, 4H), 4.9 (m, 1H), 4.3 (d, 2H), 4.0 (bs, 1H), 3.8 (bs, 1H), 3.5 (bs, 2H), 2.1 (d, 2H), 1.8 (d, 2H).

Workup

  1. customprepared by the method
  2. additionwas added
  3. stirringthe resulting mixture was stirred at room temperature overnight
  4. customthe precipitate formed
  5. customwas collected

Sources & evidence

ORD record
ord-25d7c365d12847e28472a3d7400a2ecd
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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