3-Aminopyridine → HCID 57874389, compound

HRID 1093877Notes

Reaction equation

HRID 1093877 reaction equation
CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([N:37]2[CH:41]=[C:40]([C:42]([NH:44][CH2:45][C:46]([OH:48])=O)=[O:43])[N:39]=[N:38]2)[CH:32]=1.NC1C=NC=CC=1.Cl.[NH:57]1[CH2:62][CH2:61][CH:60]([O:63][C:64]2[CH:65]=[C:66]([CH:69]=[CH:70][CH:71]=2)[C:67]#[N:68])[CH2:59][CH2:58]1>CN(C=O)C.O>[C:67]([C:66]1[CH:65]=[C:64]([CH:71]=[CH:70][CH:69]=1)[O:63][CH:60]1[CH2:61][CH2:62][N:57]([C:46](=[O:48])[CH2:45][NH:44][C:42]([C:40]2[N:39]=[N:38][N:37]([C:33]3[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=3)[CH:41]=2)=[O:43])[CH2:58][CH2:59]1)#[N:68]

Participants

9

Reactant 6

HCID 100093-AminopyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 534337453-[(Piperidin-4-yl)oxy]benzonitrile--hydrogen chloride (1/1)HCID 66592012[(1-pyridin-3-yl-1H-[1,2,3]triazole-4-carbonyl)-amino]-acetic acid

Product 1

HCID 57874389HCID 57874389, compoundYield 11.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (156.8 mg, 1.2 mmol) followed by HOBt (45 mg, 0.33 mmol) and EDCI (116 mg, 0.6 mmol) were added to a stirred solution of [(1-pyridin-3-yl-1H-[1,2,3]triazole-4-carbonyl)-amino]-acetic acid (prepared by the method used for the synthesis of Intermediate 64, starting from 3-aminopyridine, and subsequently, application of Step 3 of the General Scheme) (75 mg, 0.3 mmol) in DMF (3 mL). After 2 minutes of stirring, 3-(piperidin-4-yloxy)-benzonitrile hydrochloride (prepared by the method used for the synthesis of Intermediate 15) (72.4 mg, 0.3 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was added and formed precipitate was collected. Purification by preparative HPLC afforded 15 mg (11.5% Yield) of 1-pyridin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid {2-[4-(3-cyano-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 432.19, 99.3%. 1H NMR (300 MHz, DMSO-d6): δ 9.5 (s, 1H), 9.22 (d, 1H), 8.8 (d, 1H), 8.58 (t, 1H), 8.44 (d, 1H), 7.7 (q, 1H), 7.58-7.44 (d, 2H), 7.44 (dd, 2H), 4.8 (m, 1H), 4.3 (d, 2H), 4.0 (bs, 1H), 3.8 (d, 1H), 2.5 (b, 2H), 2.1 (t, 2H), 1.7 (bd, 2H).

Workup

  1. customprepared by the method
  2. additionwas added
  3. stirringthe resulting mixture was stirred at room temperature overnight
  4. customformed precipitate
  5. customwas collected
  6. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-d4fe8deb827648799e72eb62f18dc5f2
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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