Dichloromethane → HCID 45792086, compound

HRID 631800Notes

Reaction equation

HRID 631800 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][CH2:12][CH2:13][NH:14]C(=O)OC(C)(C)C.C(Cl)[Cl:23]>FC(F)(F)C(O)=O>[ClH:23].[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][CH2:12][CH2:13][NH2:14]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 89825709HCID 89825709, compound

Product 1

HCID 45792086HCID 45792086, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Tert-butyl N-[2-(2-quinolylamino)ethyl]carbamate (137 mg, 0.44 mmol) was dissolved in a mixture of DCM (6 ml) and trifluoroacetic acid (2 ml) and left standing at room temperature for one hour. The volatiles were removed under reduced pressure, the residue was dissolved in THF and evaporated to dryness under reduced pressure. The residue was dissolved in THF and the product was precipitated by the addition of HCl in dioxane (4N). The precipitate was removed by filtration, washed several times with THF and dried under reduced pressure to yield 55 mg of a solid (0.226 mmol, 56%) that was used directly in the next step.

Workup

  1. waitleft
  2. customThe volatiles were removed under reduced pressure
  3. dissolutionthe residue was dissolved in THF
  4. customevaporated to dryness under reduced pressure
  5. dissolutionThe residue was dissolved in THF
  6. customthe product was precipitated by the addition of HCl in dioxane (4N)
  7. customThe precipitate was removed by filtration
  8. washwashed several times with THF
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-8211e0e0dbc5403cb54e3e64fc61ae2b
Source dataset
uspto-grants-2016_04
Patent number
US09321724B2

Reaction notes

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