Water → HCID 117966289, compound

HRID 931101Notes

Reaction equation

HRID 931101 reaction equation
[CH:1]1[N:5]=[C:4]([CH:6]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]3[N:17]=[C:16]([NH2:18])[C:15]([N+:19]([O-])=O)=[CH:14][CH:13]=3)[CH2:7]2)[N:3]2[CH2:22][CH2:23][CH2:24][C:2]=12.O.[Cl-:26].[Ca+2].[Cl-]>C(O)C.[Fe]>[ClH:26].[CH:1]1[N:5]=[C:4]([CH:6]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]3[N:17]=[C:16]([NH2:18])[C:15]([NH2:19])=[CH:14][CH:13]=3)[CH2:7]2)[N:3]2[CH2:22][CH2:23][CH2:24][C:2]=12

Participants

6

Reactant 3

HCID 962WaterHCID 5284359Calcium ChlorideHCID 89853740HCID 89853740, compound

Product 1

HCID 117966289HCID 117966289, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

6-(3-(6,7-Dihydro-5H-pyrrolo[1,2-c]imidazol-3-yl)piperidin-1-yl)-3-nitropyridin-2-amine (20 mg, 0.1 mmol) was dissolved in ethanol (0.5 mL) and water (0.1 mL) under nitrogen. Then iron 200 mesh (27 mg, 0.5 mmol) and calcium chloride (3.3 mg, 0.03 mmol) were added and the mixture was heated to 70° C. for 18 h. The reaction mixture was cooled to room temperature followed by filtration through a 0.2 μm nylon syringe filter and rinsing with ethanol (0.5 mL) to afford the title compound. The filtrate was carried on to the next step without further purification. MS (AP+) (M+H) 299.1; LCMS retention time: 0.44 minutes (Method L)

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfollowed by filtration through a 0.2 μm nylon syringe
  3. filtrationfilter
  4. washrinsing with ethanol (0.5 mL)

Sources & evidence

ORD record
ord-f4e48f74565346fcabc86cb3188d1261
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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