Water → HCID 57962617, compound

HRID 541928Notes

Reaction equation

HRID 541928 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-])=O)[CH:25]=3)[CH:17]=2)[C:12]([Cl:33])=[CH:11][N:10]=1.O>CO.C(O)(=O)C.[Fe]>[NH2:30][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[CH2:23][NH:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([NH:15][C:13]2[C:12]([Cl:33])=[CH:11][N:10]=[C:9]([Cl:8])[N:14]=2)[CH:17]=1

Participants

6

Reactant 2

HCID 962WaterHCID 86636291HCID 86636291, compound

Product 1

HCID 57962617HCID 57962617, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalyst2×HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of N-(2,5-dichloropyrimidin-4-yl)-N′-(3-nitrobenzyl)benzene-1,3-diamine trifluoroacetate (67 mg, 0.13 mmol) in methanol (0.51 mL), acetic acid (0.20 mL), and water (0.10 mL) was treated with iron (30 mg, 0.53 mmol) and stirred at 25° C. for 1 h. The reaction mixture was treated with additional iron (25 mg, 0.45 mmol) and stirred at 25° C. for 16 h. The reaction mixture was diluted with methanol (2 mL) and celite was added. The resulting suspension was filtered through a pad of celite and rinsed with methanol. The filtrate was concentrated to give the desired product as a crude residue that was used without further purification.

Workup

  1. stirringstirred at 25° C. for 16 h
  2. additionwas added
  3. filtrationThe resulting suspension was filtered through a pad of celite
  4. washrinsed with methanol
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b31f4435e9754961a0e03c849eb1fbcb
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

Loading…