Triethylamine → HCID 57982676, compound

HRID 1868401Notes

Reaction equation

HRID 1868401 reaction equation
[OH:1][CH:2]([CH3:25])[CH2:3][NH:4][C:5]([C:7]1[C:8]([C:21]([F:24])([F:23])[F:22])=[N:9][C:10]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)=[N:11][CH:12]=1)=[O:6].C(N(CC)CC)C>CS(C)=O.ClCCl>[O:1]=[C:2]([CH3:25])[CH2:3][NH:4][C:5]([C:7]1[C:8]([C:21]([F:22])([F:24])[F:23])=[N:9][C:10]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)=[N:11][CH:12]=1)=[O:6]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 59191142HCID 59191142, compound

Product 1

HCID 57982676HCID 57982676, compoundYield 45.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(3-chloro-phenylamino)-trifluoromethyl-pyrimidine-5-carboxylic acid (2-hydroxy-propyl)-amide (200 mg) in dimethylsulfoxide (6.0 ml) and triethylamine (324 mg) at 0° C. was added a solution of sulphur trioxide-pyridine complex (250 mg) in dimethylsulfoxide (6.0 ml). This was allowed to warm to room temperature and after 2 hours the mixture was diluted with dichloromethane and washed twice with 0.1N hydrochloric acid. The organic layer was dried (Na2SO4) and evaporated. The sample was purified by mass directed auto-purification to afford the title compound (91 mg).

Workup

  1. washwashed twice with 0.1N hydrochloric acid
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated
  4. customThe sample was purified by mass
  5. customauto-purification

Sources & evidence

ORD record
ord-e62937d4e4744f69b33b0a9dc82d14a5
Source dataset
uspto-grants-2009_12
Patent number
US07635701B2

Reaction notes

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