3-Aminopyridine → HCID 66591633, compound

HRID 1093790Notes

Reaction equation

HRID 1093790 reaction equation
CCN(C(C)C)C(C)C.[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[CH:20]=[C:19]([C:21]([OH:23])=O)[N:18]=[N:17]2)[CH:11]=1.NC1C=NC=CC=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:53][CH2:54][C:55]([N:57]1[CH2:62][CH2:61][CH:60]([O:63][C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][C:65]=2[Cl:70])[CH2:59][CH2:58]1)=[O:56]>CN(C=O)C.O>[Cl:70][C:65]1[CH:66]=[CH:67][CH:68]=[CH:69][C:64]=1[O:63][CH:60]1[CH2:59][CH2:58][N:57]([C:55](=[O:56])[CH2:54][NH:53][C:21]([C:19]2[N:18]=[N:17][N:16]([C:12]3[CH:11]=[N:10][CH:15]=[CH:14][CH:13]=3)[CH:20]=2)=[O:23])[CH2:62][CH2:61]1

Participants

9

Reactant 6

HCID 100093-AminopyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 44454552933737-38-3HCID 665915282-Amino-1-[4-(2-chloro-phenoxy)-piperidin-1-yl]-ethanone hydrochloride

Product 1

HCID 66591633HCID 66591633, compoundYield 90.74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (215 mg, 1.66 mmol) was added to a stirred solution of 1-pyridin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid (70 mg, 0.37 mmol) (prepared by the method used for the synthesis of Intermediate 64, starting from 3-aminopyridine) in DMF (5 mL) followed by HOBt (55 mg, 0.41 mmol) and EDCI (177 mg, 0.92 mmol) and stirring was continued at ambient temperature. After 2 minutes of stirring, 2-amino-1-[4-(2-chloro-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (prepared according to Step 1 and 5 of the General Scheme) (124 mg, 0.4 mmol) was added and the resulting mixture was stirred at ambient temperature overnight. Cold water was then added and filtered the precipitate was filtered to afford 147 mg (90.74% Yield) of 1-pyridin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 441, 98.31%. 1H NMR (300 MHz, DMSO-d6): δ 9.5 (s, 1H), 9.24 (d, 1H), 8.76 (d, 1H), 8.56 (t, 1H), 8.46 (d, 1H), 7.74 (d, 1H), 7.48 (d, 1H), 7.36 (q, 2H), 7.02 (t, 1H), 4.8 (m, 1H), 4.4 (d, 2H), 3.8 (t, 2H), 3.6 (t, 2H), 2.1 (d, 2H), 1.8 (d, 2H).

Workup

  1. customprepared by the method
  2. customwas continued at ambient temperature
  3. stirringAfter 2 minutes of stirring
  4. additionwas added
  5. stirringthe resulting mixture was stirred at ambient temperature overnight
  6. filtrationfiltered the precipitate
  7. filtrationwas filtered

Sources & evidence

ORD record
ord-4c386c4f4d5442cdb3013a82d2b41afa
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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