Trifluoroacetic acid → HCID 25230478, compound

HRID 1961711Notes

Reaction equation

HRID 1961711 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[N:14]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:15]1[CH:20]=[N:19][CH:18]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=2)[N:16]=1)(C)(C)C.[OH-].[NH4+]>ClCCl>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([NH:14][C:15]2[CH:20]=[N:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=3)[N:16]=2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 59570656(4-Chloro-phenyl)-[6-(6-methyl-pyridin-2-yl)-pyrazin-2-yl]-carbamic acid tert-butyl ester

Product 1

HCID 25230478HCID 25230478, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (1.0 mL, 13.4 mmol) in dichloromethane (3 mL) was added to an ice cooled solution of (4-chloro-phenyl)-[6-(6-methyl-pyridin-2-yl)-pyrazin-2-yl]-carbamic acid tert-butyl ester (70 mg, 0.18 mmol) in dichloromethane (4 mL) and stirred for 2.5 hour at room temperature. The reaction mixture was cooled on an ice bath and aqueous ammonium hydroxide was added followed by evaporation of dichloromethane. The formed precipitate was filtered off. The crude product was purified by flash chromatography (ethyl acetate/heptane as eluent) to give (4-chloro-phenyl)-[6-(6-methyl-pyridin-2-yl)-pyrazin-2-yl]-amine (51 mg, 98%).

Workup

  1. temperatureThe reaction mixture was cooled on an ice bath
  2. customfollowed by evaporation of dichloromethane
  3. filtrationThe formed precipitate was filtered off
  4. customThe crude product was purified by flash chromatography (ethyl acetate/heptane as eluent)

Sources & evidence

ORD record
ord-e8c739f8155640c88de1026446b71d5f
Source dataset
uspto-grants-2013_04
Patent number
US08415358B2

Reaction notes

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