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

HRID 1093663Notes

Reaction equation

HRID 1093663 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.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.Cl.[NH:54]1[CH2:59][CH2:58][CH:57]([NH:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][C:62]=2[Cl:67])[CH2:56][CH2:55]1>CN(C=O)C.O>[Cl:67][C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][C:61]=1[NH:60][CH:57]1[CH2:58][CH2:59][N:54]([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])[CH2:55][CH2:56]1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57874471[(5-Phenylamino-pyridine-2-carbonyl)-amino]-acetic acidHCID 66591362HCID 66591362, compound

Product 1

HCID 442332655-Phenylamino-pyridine-2-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amideYield 64%

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 piperidin-4-yl-(2-chloro-phenyl)-amine dihydrochloride (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 0.038 g (64%) of 5-phenylamino-pyridine-2-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 464.18 (M+1)+, 92.88%, 1H NMR (DMSO-d6): δ 8.9 (s, 1H), 8.5 (t, 1H), 8.3 (d, 1H), 7.9 (d, 1H), 7.55 (dd, 1H), 7.35 (t, 2H), 7.2 (m, 4H), 7.0 (t, 1H), 6.9 (d, 1H), 6.6 (t, 1H), 4.9 (d, 1H), 4.35 (d, 1H), 4.2 (d, 2H), 3.85 (d, 1H), 3.55 (s, 1H), 3.2 (m, 2H), 2.85 (m, 1H), 1.95 (t, 2H), 1.5 (m, 1H), 1.35 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-12cf79792d6a4df4872086b0033a4e32
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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