Trifluoroacetic acid → HCID 19592871, compound

HRID 613528Notes

Reaction equation

HRID 613528 reaction equation
C(OC([NH:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1)=[CH:16][CH:15]=[CH:14][C:13]=2[NH:24][C:25](=[O:34])[C:26]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:33])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1)=[CH:16][CH:15]=[CH:14][C:13]=2[NH:24][C:25](=[O:34])[C:26]1[C:27]([Cl:33])=[CH:28][CH:29]=[CH:30][C:31]=1[Cl:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19592482HCID 19592482, compound

Product 1

HCID 19592871HCID 19592871, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-tert-butoxycarbonylamino-8-(2,6-dichlorobenzoylamino)-4-(imidazol-1-yl)quinoline (869 mg) in dichloromethane (2 ml) was added trifluoroacetic acid (5 ml) under ice-cooling, and the mixture was stirred for 2 hours at ambient temperature. The mixture was partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from isopropyl alcohol to give 3-amino-8-(2,6-dichlorobenzoylamino)-4-(imidazol-1-yl)quinoline (581.4 mg).

Workup

  1. temperaturecooling
  2. customThe mixture was partitioned between dichloromethane and saturated sodium bicarbonate solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was crystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-4c6ac2ba4a8a4d488771b7bebb89159b
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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