Ammonium Chloride → HCID 10270834, compound

HRID 1815190Notes

Reaction equation

HRID 1815190 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[C:15]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:13])=[CH:7][C:6]=1[N+:28]([O-])=O)([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:28][C:6]1[CH:7]=[C:8]([NH:11][C:12]([C:14]2[C:15]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:13])[CH:9]=[CH:10][C:5]=1[C:1]([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 10222947HCID 10222947, compound

Product 1

HCID 10270834HCID 10270834, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-[4-(tert-butyl)-3-nitrophenyl]{2-[(2-pyridylmethyl)amino](3-pyridyl)}carboxamide (100 mg, 0.25 mmol, Example 73), iron powder (69 mg, 1.25 mmol) and NH4Cl (10 mg, 0.17 mmol) in EtOH (0.5 mL) and H2O (0.5 ml) was stirred for 4 h at 80° C. The reaction mixture was filtered, concentrated, and purified through column chromatography to give the product. MS (ES+):376 M+H); (ES−):374(M−H). Calc'd. for C22H25N5O—375.21.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. custompurified through column chromatography
  4. customto give the product

Sources & evidence

ORD record
ord-aa384890c8704eda8739e6817026d5cc
Source dataset
uspto-grants-2005_04
Patent number
US06878714B2

Reaction notes

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