Hydrochloric Acid → N-(2-aminoethyl)-5-(2-chloro-5-(3-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxamide

HRID 522086Notes

Reaction equation

HRID 522086 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:22]([C:25]2[C:30]([F:31])=[CH:29][CH:28]=[CH:27][N:26]=2)=[CH:21][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[C:9]([C:18](O)=[O:19])[CH:8]=1)=[O:5].C(OC(=O)[NH:38][CH2:39][CH2:40][NH2:41])(C)(C)C.Cl>C(Cl)Cl.O1CCOCC1>[NH2:38][CH2:39][CH2:40][NH:41][C:18]([C:9]1[CH:8]=[C:7]([NH:6][C:4](=[O:5])[C:3]2[CH:21]=[C:22]([C:25]3[C:30]([F:31])=[CH:29][CH:28]=[CH:27][N:26]=3)[CH:23]=[CH:24][C:2]=2[Cl:1])[N:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=1)=[O:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 187201N-BOC-ethylenediamineHCID 1184971095-(2-chloro-5-(3-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid

Product 1

HCID 118497081N-(2-aminoethyl)-5-(2-chloro-5-(3-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared according to the method described for Example 3 using 5-(2-chloro-5-(3-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid (Example 105) and tert-butyl(2-aminoethyl)carbamate. The residue was dissolved in DCM (10 mL) and treated with 4M HCl in dioxane (5 mL) with stirring at room temperature for 4 hours. The reaction was concentrated in vacuo and eluted through an SCX-2 column using MeOH followed by 7N NH3 in MeOH; followed by reverse phase chromatography eluting with 5-95% MeCN (with 0.1% NH3) in water (with 0.1% NH3); followed by silica gel column chromatography eluting with 1-5% 7N NH3/MeOH in DCM and finally trituration with TBME.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. washeluted through an SCX-2 column
  3. washeluting with 5-95% MeCN (with 0.1% NH3) in water (with 0.1% NH3)
  4. washeluting with 1-5% 7N NH3/MeOH in DCM and finally trituration with TBME

Sources & evidence

ORD record
ord-32dcca044d1942248a6de9b54cb76547
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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