Hydrochloric Acid → HCID 86620292, compound

HRID 2043344Notes

Reaction equation

HRID 2043344 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[C:7]([F:22])=[C:8]([N:13]([CH2:20][CH3:21])[CH2:14][C:15]2[NH:16][CH:17]=[N:18][CH:19]=2)[CH:9]=[CH:10][C:11]=1[F:12].Cl>O1CCCC1>[CH2:20]([N:13]([CH2:14][C:15]1[NH:16][CH:17]=[N:18][CH:19]=1)[C:8]1[C:7]([F:22])=[C:6]([C:11]([F:12])=[CH:10][CH:9]=1)[CH:2]=[O:1])[CH3:21]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66751231HCID 66751231, compound

Product 1

HCID 86620292HCID 86620292, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (3-[1,3]dioxolan-2-yl-2,4-difluoro-phenyl)-ethyl-(3H-imidazol-4-ylmethyl)-amine (0.22 g, 0.70 mmol) in tetrahydrofuran (5 ml) was added a 3 N aqueous solution of hydrochloric acid (0.93 ml, 2.79 mmol) and the mixture was stirred at room temperature for 48 h. The mixture was then concentrated in vacuo and the residue taken up in ethyl acetate and washed with 1 N aq. sodium hydroxide solution. The layers were separated and the aqueous phase was back extracted twice with ethyl acetate. The combined organic phases were washed with saturated brine, then dried over magensium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (column: Isolute® Flash-NH2 (Separtis); eluent: methanol/dichloromethane gradient) to yield a yellow gum (111 mg, 48%); MS (ISP): 266.0 ((M+H)+.).

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. washwashed with 1 N aq. sodium hydroxide solution
  3. customThe layers were separated
  4. extractionthe aqueous phase was back extracted twice with ethyl acetate
  5. washThe combined organic phases were washed with saturated brine
  6. dry with materialdried over magensium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (column: Isolute® Flash-NH2 (Separtis); eluent: methanol/dichloromethane gradient)

Sources & evidence

ORD record
ord-7f15591ff67a41f780deee29d18b170d
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

Loading…