1-Hydroxybenzotriazole → 5-Phenylamino-pyridine-2-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide

HRID 1093664Notes

Reaction equation

HRID 1093664 reaction equation
[C:1]1([NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]([NH:16][CH2:17][C:18]([OH:20])=O)=[O:15])=[N:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[CH:30]1[CH:31]=[CH:32][C:33]2N(O)N=[N:36][C:34]=2[CH:35]=1.CCN=C=NCCCN(C)C.[ClH:51].Cl.ClC1C=CC=CC=1O[CH:57]1[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]1>CN(C=O)C.O>[Cl:51][C:33]1[CH:32]=[CH:31][CH:30]=[CH:35][C:34]=1[NH:36][CH:57]1[CH2:62][CH2:61][N:60]([C:18](=[O:20])[CH2:17][NH:16][C:14]([C:11]2[CH:10]=[CH:9][C:8]([NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:13][N:12]=2)=[O:15])[CH2:59][CH2:58]1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 167325894-(2-Chlorophenoxy)piperidine hydrochlorideHCID 57874471[(5-Phenylamino-pyridine-2-carbonyl)-amino]-acetic acid

Product 1

HCID 442332655-Phenylamino-pyridine-2-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amideYield 53.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of [(5-phenylamino-pyridine-2-carbonyl)-amino]-acetic acid (0.035 g, 0.00013 mol) in DMF (1 mL) was added DIPEA (0.05 g, 0.00039 mol), HOBt (0.0209 g, 0.00015 mol) and EDCI.HCl (0.0296 g, 0.00015 mol) at ambient temperature. After 2 minutes 4-(2-chloro-phenoxy)-piperidine hydrochloride (0.0382 g, 0.00015 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the resulting precipitate was isolated by filtration and dried to afford 0.032 g (53%) of 5-phenylamino-pyridine-2-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 465.16 (M+1)+, 98.06%, 1H NMR (DMSO-d6): δ 8.85 (s, 1H), 8.5 (t, 1H), 8.35 (d, 1H), 7.85 (d, 1H), 7.55 (dd, 1H), 7.4 (d, 1H), 7.3 (m, 4H), 7.2 (d, 2H), 7.0 (m, 2H), 4.75 (m, 1H), 4.2 (d, 2H), 3.7 (m, 2H), 3.5 (m, 2H), 1.95 (m, 3H), 1.7 (m, 2H).

Workup

  1. customthe resulting precipitate was isolated by filtration
  2. customdried

Sources & evidence

ORD record
ord-31bc87ab845540d1b8afdd6e04105b64
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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