1,2-Dichloroethane → HCID 10163705, compound

HRID 2109610Notes

Reaction equation

HRID 2109610 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11]3[C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=[CH:13][N:12]=3)[CH:8]=2)[CH:3]=[N:2]1.[F:20][C:21]([F:36])([F:35])[C:22]([C:28]1[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=1)([OH:27])[C:23]([F:26])([F:25])[F:24].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11]3[C:16]([C:17]([NH:34][C:31]4[CH:30]=[CH:29][C:28]([C:22]([OH:27])([C:21]([F:20])([F:35])[F:36])[C:23]([F:24])([F:25])[F:26])=[CH:33][CH:32]=4)=[O:19])=[CH:15][CH:14]=[CH:13][N:12]=3)[CH:8]=2)[CH:3]=[N:2]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 5778012-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-olHCID 21959407HCID 21959407, compound

Product 1

HCID 10163705HCID 10163705, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-(1H-Indazol-6-ylamino)pyridine-3-carboxylic acid (500 mg, Step A) was reacted with 4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenylamine (340 mg) and EDC (500 mg) and HOBt (270 mg) in DMF at RT overnight. The reaction was diluted with CH2Cl2 and washed with H2O followed by brine. The organic layer was dried with Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography to give the title compound. MS (ES+): 496(M+H)+; (ES−): 394(M−H). Calc'd. for C22H15F6N5O2−495.1.

Workup

  1. washwashed with H2O
  2. dry with materialThe organic layer was dried with Na2SO4
  3. customevaporated under reduced pressure
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-167eba54c9e7412d94c75ac696166ae1
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

Loading…