Hydrochloric Acid → HCID 178448790, compound

HRID 869143Notes

Reaction equation

HRID 869143 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:27])([CH3:26])[CH2:9][NH:10][C:11]2[N:16]=[N:15][C:14]([C:17]3[N:18]=[C:19]([NH:22]C(=O)C)[NH:20][CH:21]=3)=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.Cl>CO>[NH2:22][C:19]1[NH:20][CH:21]=[C:17]([C:14]2[N:15]=[N:16][C:11]([NH:10][CH2:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)([CH3:27])[CH3:26])=[CH:12][CH:13]=2)[N:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178474422HCID 178474422, compound

Product 1

HCID 178448790HCID 178448790, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 10 mL round bottom flask was added N-(4-(6-(2-(4-fluorophenyl)-2-methylpropylamino)pyridazin-3-yl)-1H-imidazol-2-yl)acetamide (22 mg, 59 μmol), concentrated HCl (100 μL) and methanol (1 mL). The reaction was refluxed for 12 h and then concentrated, redissolved in EtOAc (10 mL), washed with saturated sodium carbonate (2×10 mL) and brine (1×10 mL), dried (Na2SO4) and concentrated to yield 8 mg (42%) of 6-(2-amino-1H-imidazol-4-yl)-N-(2-(4-fluorophenyl)-2-methylpropyl)pyridazin-3-amine as a pale yellow solid, m/z=327.2 [M+H].

Workup

  1. temperatureThe reaction was refluxed for 12 h
  2. concentrationconcentrated
  3. dissolutionredissolved in EtOAc (10 mL)
  4. washwashed with saturated sodium carbonate (2×10 mL) and brine (1×10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-65de65ce713a437f9e24bc4f7f411014
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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