1-Hydroxybenzotriazole → HCID 178523486, compound

HRID 1093633Notes

Reaction equation

HRID 1093633 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[C:10]([C:13]([OH:15])=O)[CH:9]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.Cl.[NH2:49][CH2:50][C:51]([N:53]1[CH2:58][CH2:57][CH:56]([NH:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=2[Cl:66])[CH2:55][CH2:54]1)=[O:52]>CN(C=O)C.O>[Cl:66][C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][C:60]=1[NH:59][CH:56]1[CH2:55][CH2:54][N:53]([C:51](=[O:52])[CH2:50][NH:49][C:13]([C:10]2[CH:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=3)[NH:12][N:11]=2)=[O:15])[CH2:58][CH2:57]1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 665917512-Amino-1-[4-(2-chloro-phenylamino)-piperidin-1-yl]-ethanone dihydrochlorideHCID 178524130HCID 178524130, compound

Product 1

HCID 178523486HCID 178523486, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-(4-hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid (0.1 g, 0.00049 mol) in DMF (5 mL) was added DIPEA (0.253 g, 0.00196 mol), HOBt (0.0827 g, 0.00061 mol) and EDCI.HCl (0.117 g, 0.00061 mol) at ambient temperature. After 5 minutes 2-amino-1-[4-(2-chloro-phenylamino)-piperidin-1-yl]-ethanone dihydrochloride (0.164 g, 0.00054 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water. The resulting precipitate was isolated by filtration and recrystallized from ethyl acetate to afford 0.092 g (41%) of 5-(4-hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 426.16 (M+1)+, 91.47%, 1H NMR (DMSO-d6): δ 13.5 (s, 1H), 9.7 (s, 1H), 8.0 (s, 1H), 7.58 (d, 2H), 7.1 (m, 2H), 6.8 (m, 4H), 6.56 (m, 1H), 4.9 (d, 1H), 4.3 (d, 1H), 4.1 (d, 2H), 3.8 (m, 11H), 3.6 (m, 11H), 3.1 (m, 1H), 2.7 (m, 1H), 1.9 (m, 2H), 1.3 (m, 2H)

Workup

  1. customThe resulting precipitate was isolated by filtration
  2. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1fa1af20be4042a88a4350a366a9ef22
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

Loading…