Diisopropylethylamine → HCID 178523485, compound

HRID 1093619Notes

Reaction equation

HRID 1093619 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[NH:19][N:18]=[C:17]([C:20]([NH:22][CH2:23][C:24](O)=[O:25])=[O:21])[CH:16]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.Cl.Cl.[Cl:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[NH:57][CH:58]1[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]1>CN(C=O)C.O>[Cl:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[NH:57][CH:58]1[CH2:63][CH2:62][N:61]([C:24](=[O:25])[CH2:23][NH:22][C:20]([C:17]2[CH:16]=[C:15]([C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:10]=3)[NH:19][N:18]=2)=[O:21])[CH2:60][CH2:59]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66591362HCID 66591362, compoundHCID 178525881HCID 178525881, compound

Product 1

HCID 178523485HCID 178523485, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of {[5-(3-benzyloxy-phenyl)-1H-pyrazole-3-carbonyl]-amino}-acetic acid (0.15 g, 0.00039 mol) in DMF (2 mL) was added DIPEA (0.224 g, 0.00174 mol) HOBt (0.065 g, 0.000482 mol) and EDCI.HCl (0.0925 g, 0.00048 mol) at ambient temperature. After 5 minutes (2-chloro-phenyl)-piperidin-4-yl-amine dihydrochloride (0.1 g, 0.00041 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. Purification by column chromatography using basic aluminium oxide (60% ethyl acetate in hexane) afforded 0.19 g (91%) of 5-(3-benzyloxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 544.2 (M+1)+, 96.18%.

Workup

  1. customThe resulting precipitate was isolated by filtration
  2. customPurification by column chromatography

Sources & evidence

ORD record
ord-f876a5e5b5534383b210f64865658959
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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